S-methyl chlorothioformate → [(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-thiocarbamic acid S-methyl ester

HRID 1992428Notes

Reaction equation

HRID 1992428 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:16]([NH2:24])[C:17]2[C:22]([Cl:23])=[N:21][CH:20]=[CH:19][N:18]=2)[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:34][S:35][C:36](=[O:38])Cl>ClCCl.CCOC(C)=O>[CH3:34][S:35][C:36](=[O:38])[NH:24][CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:11]=1)[C:17]1[C:22]([Cl:23])=[N:21][CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 3

HCID 17772S-methyl chlorothioformateHCID 81531DiisopropylethylamineHCID 86604615C-(3-benzyloxyphenyl)-C-(3-chloropyrazin-2-yl)methylamine hydrochloride

Product 1

HCID 58902032[(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-thiocarbamic acid S-methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of C-(3-benzyloxy-phenyl)-C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride salt (3.10 g, 0.00856 mol) in dichloromethane (30 mL) were added N,N-diisopropylethylamine (2.98 mL, 0.0171 mol) and carbonochloridothioic acid S-methyl ester (946 mg, 0.00856 mol) at 0° C. After 5 min, the mixture was warmed to rt and stirred overnight. The mixture was diluted with EtOAc (100 mL), washed with water (20 mL), sat. aq. NaHCO3 (2×30 mL), brine (30 mL), and dried over anhydrous sodium sulfate. The crude product was purified by silical gel chromatogrphy (Hex: EtOAc=70:30→60:40) to give the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 2.34 (s, 3H), 5.03 (s, 2H), 6.53 (d, J=6.8 Hz, 1H), 6.87-6.97 (m, 3H), 7.08 (d, J=7.7 Hz, 1H), 7.22 (d, J=7.7 Hz, 1H), 7.30-7.41 (m, 5H), 8.33 (d, J=2.4 Hz, 1H), 8.51 (d, J=2.4 Hz, 1H).

Workup

  1. washwashed with water (20 mL), sat. aq. NaHCO3 (2×30 mL), brine (30 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe crude product was purified by silical gel chromatogrphy (Hex: EtOAc=70:30→60:40)

Sources & evidence

ORD record
ord-d4c730e9f26946558c13cd650ebe467e
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

Loading…