Development of a Nitrene-Type Rearrangement for the Commercial Route of the JAK1 Inhibitor Abrocitinib
Connor, Christina G.; DeForest, Jacob C.; Dietrich, Phil; Do, Nga M.; Doyle, Kevin M.; Eisenbeis, Shane; Greenberg, Elizabeth; Griffin, Sarah H.; Jones, Brian P.; Jones, Kris N.; Karmilowicz, Michael; Kumar, Rajesh; Lewis, Chad A.; McInturff, Emma L.; McWilliams, J. Christopher; Mehta, Ruchi; Nguyen, Bao D.; Rane, Anil M.; Samas, Brian; Sitter, Barbara J.; Ward, Howard W.; Webster, Mark E.; Organic Process Research & Development  (2020) –; doi:10.1021/acs.oprd.0c00366

data_1559125
_publ_section_title
;
 Development of a Nitrene-Type Rearrangement for the Commercial Route of
 the JAK1 Inhibitor Abrocitinib
;
_journal_name_full               'Organic Process Research &amp; Development'
_journal_paper_doi               10.1021/acs.oprd.0c00366
_journal_year                    2020
_chemical_formula_sum            'C11 H18 N5 O4 P'
_chemical_formula_weight         315.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.771(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5143(7)
_cell_length_b                   26.599(3)
_cell_length_c                   7.9568(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1349.7(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22550
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.531
_diffrn_reflns_theta_min         3.323
_exptl_absorpt_coefficient_mu    2.063
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.721
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.723
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1921
_reflns_number_total             2542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op0c00366_si_002.cif
_cod_data_source_block           ZZ953
_cod_original_cell_volume        1349.7(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559125
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.852
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              94857
_shelx_hkl_checksum              49345