Biomass-involved synthesis of N-substituted benzofuro[2,3-d]pyrimidine-4-amines and biological evaluation as novel EGFR tyrosine kinase inhibitors
Zou, Yong; Sheng, Jianfei; Liu, Zhihong; Yan, Ming; Zhang, Xue-jing; Wang, Dejian; Xu, Jun; Zhang, Ensheng; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00793K

data_7155628
_publ_section_title
;
 Biomass-involved synthesis of N-substituted
 benzofuro[2,3-d]pyrimidine-4-amines and biological evaluation as novel
 EGFR tyrosine kinase inhibitors
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00793K
_journal_year                    2017
_chemical_formula_moiety         'C19 H15 N3 O4'
_chemical_formula_sum            'C19 H15 N3 O4'
_chemical_formula_weight         349.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-06 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                110.700(5)
_cell_angle_beta                 100.085(4)
_cell_angle_gamma                101.913(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7171(4)
_cell_length_b                   10.6392(6)
_cell_length_c                   11.0090(4)
_cell_measurement_reflns_used    4732
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.0620
_cell_measurement_theta_min      4.9340
_cell_volume                     796.35(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.9544
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -63.00  20.00   1.00    2.00    --  -44.52  57.00  60.00   83
  2  \w     75.00 117.00   1.00    2.00    --   44.52 125.00-150.00   42
  3  \w    138.00 171.00   1.00    4.00    --  100.00  30.00-120.00   33
  4  \w    102.00 128.00   1.00    4.00    --  100.00  30.00-120.00   26
  5  \w     39.00 120.00   1.00    4.00    --  100.00 -45.00 -90.00   81
  6  \w     74.00  99.00   1.00    4.00    --  100.00-125.00 -90.00   25
  7  \w     40.00 101.00   1.00    4.00    --  100.00 -94.00   0.00   61
  8  \w     28.00 116.00   1.00    4.00    --  100.00-125.00 -30.00   88
  9  \w     36.00 118.00   1.00    4.00    --  100.00-125.00-150.00   82
 10  \w     27.00 100.00   1.00    4.00    --  100.00 -77.00  60.00   73
 11  \w     33.00 118.00   1.00    4.00    --  100.00 -45.00 150.00   85
 12  \w     92.00 162.00   1.00    4.00    --  100.00  45.00 120.00   70
 13  \w     21.00  89.00   1.00    2.00    --   44.52  57.00-180.00   68
 14  \w    -52.00 -26.00   1.00    4.00    --  -90.00  45.00-150.00   26
 15  \w   -105.00 -79.00   1.00    4.00    --  -90.00  45.00-150.00   26
 16  \w   -114.00 -20.00   1.00    2.00    --  -44.52 -57.00 -90.00   94
 17  \w   -168.00 -51.00   1.00    4.00    --  -90.00 -15.00   0.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1907092000
_diffrn_orient_matrix_UB_12      -0.0038465000
_diffrn_orient_matrix_UB_13      0.0665959000
_diffrn_orient_matrix_UB_21      -0.0718679000
_diffrn_orient_matrix_UB_22      -0.1611032000
_diffrn_orient_matrix_UB_23      -0.0529003000
_diffrn_orient_matrix_UB_31      0.0582332000
_diffrn_orient_matrix_UB_32      -0.0146414000
_diffrn_orient_matrix_UB_33      -0.1300733000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6140
_diffrn_reflns_theta_full        67.0733
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.97
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4568
_exptl_crystal_description       block
_exptl_crystal_F_000             365.2760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4231
_refine_diff_density_min         -0.4943
_refine_diff_density_rms         0.0459
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             8.8953
_refine_ls_goodness_of_fit_ref   1.0489
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0489
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.2672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2585
_reflns_number_total             2817
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7ob00793k2.cif
_cod_data_source_block           sjf_161228_2
_cod_database_code               7155628
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C14(H14), C19(H19), C17(H17), C23(H23), C10(H10), C13(H13), N4(H4),
 C11(H11)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C26(H26a,H26b,H26c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.143
_oxdiff_exptl_absorpt_empirical_full_min 0.526