Synthesis of 3-Aminopyrazinone Mediated by 2-Pyridylthioimidate-ZnCl~2~ Complexes. Development of an Efficient Route to a Thrombin Inhibitor
John Y. L. Chung; Raymond J. Cvetovich; Fuh-Rong Tsay; Peter G. Dormer; Lisa DiMichele; David J. Mathre; Jennifer R. Chilenski; Bing Mao; Robert Wenslow; Journal of Organic Chemistry 68 (2003) 8838–8846; doi:10.1021/jo034835e

data_4022532
_publ_contact_author_address
;    Process Research
    Merck Research Laboratories
    P.O. Box 2000
    Rahway, NJ 07065
    USA
;
_publ_contact_author_email       john_chung@merck.com
_publ_contact_author_name        'John Y. L. Chung'
_publ_section_title
;
 Synthesis of 3-Aminopyrazinone Mediated by
 2-Pyridylthioimidate-ZnCl~2~ Complexes.
 Development of an Efficient Route to a Thrombin Inhibitor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8838
_journal_page_last               8846
_journal_paper_doi               10.1021/jo034835e
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C13 H13 Cl2 N3 O3 S Zn, C2 H3 N'
_chemical_formula_sum            'C15 H16 Cl2 N4 O3 S Zn'
_chemical_formula_weight         468.65
_chemical_name_common            'Compound 31'
_chemical_name_systematic
;     [2-oxo-3-(pyridin-2-ylthio)pyrazin-1(2H)-yl]acetate 
    Zinc Dichloride Complex 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.410(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.959(7)
_cell_length_b                   14.202(6)
_cell_length_c                   8.757(4)
_cell_measurement_temperature    298(2)
_cell_volume                     1984.2(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0813
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9519
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.981
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0747P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                2187
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034835esi20030616_034622.cif
_cod_data_source_block           compound31
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022532