Selective C-Acylation of 2-Aminoimidazo[1,2-a]pyridine: Application to the Synthesis of Imidazopyridine-Fused [1,3]Diazepinones
Nicolas Masurier; Roberta Aruta; Vincent Gaumet; Séverine Denoyelle; Emmanuel Moreau; Vincent Lisowski; Jean Martinez; Ludovic T. Maillard; Journal of Organic Chemistry 77 (2012) 3679–3685; doi:10.1021/jo300364d

data_4027144
_publ_contact_author_address
;
Institut des biomol\'ecules Max Mousseron
UMR 5247, CNRS, Universit\'es Montpellier I et II
UFR des Sciences Pharmaceutiques et Biologiques
15 Avenue Charles Flahault
34093 Montpellier Cedex 5
France
;
_publ_contact_author_email       nicolas.masurier@univ-montp1.fr
_publ_contact_author_name        'Nicolas Masurier'
_publ_section_title
;
 Selective C-Acylation of 2-Aminoimidazo[1,2-a]pyridine: Application to
 the Synthesis of Imidazopyridine-Fused [1,3]Diazepinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3679
_journal_page_last               3685
_journal_paper_doi               10.1021/jo300364d
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C23 H19 N5 O3, 0.5(C H2 Cl2)'
_chemical_formula_moiety         'C23 H19 N5 O3, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C23.5 H20 Cl N5 O3'
_chemical_formula_weight         455.90
_chemical_melting_point          416.3
_chemical_name_common
; 
(2R,4S)-4-benzyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydro
-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one
;
_chemical_name_systematic
; 
(2R,4S)-4-benzyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydro
-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.038(2)
_cell_length_b                   7.2524(6)
_cell_length_c                   13.9045(13)
_cell_measurement_reflns_used    1138
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.89
_cell_measurement_theta_min      3.07
_cell_volume                     2222.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5482
_diffrn_reflns_theta_full        19.98
_diffrn_reflns_theta_max         19.98
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
The unit cell contains two methylene chlorine molecules 
which have been treated as a diffuse contribution to the 
overall scattering without specific atom positions 
by SQUEEZE/PLATON. 
;
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0842
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1909P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.2567
_reflns_number_gt                1586
_reflns_number_total             2035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300364d_si_001.cif
_cod_data_source_block           C23#RS
_cod_original_cell_volume        2222.4(4)
_cod_original_formula_sum        'C23.5 H20 Cl1 N5 O3'
_cod_database_code               4027144