2-Chloroethyl Isothiocyanate → 1-Benzyl-N-(3,4-difluorobenzyl)-6-(4,5-dihydrothiazol-2-ylamino)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

HRID 40150

Reaction equation

HRID 40150 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=3)=[O:22])=[C:7]([CH:18]([CH3:20])[CH3:19])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:33].Cl[CH2:35][CH2:36][N:37]=[C:38]=[S:39]>C(Cl)Cl.CCN(CC)CC>[CH2:11]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([F:33])=[C:2]([NH:1][C:38]3[S:39][CH2:35][CH2:36][N:37]=3)[CH:10]=2)[C:6]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)=[O:22])=[C:7]1[CH:18]([CH3:19])[CH3:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 1386612-Chloroethyl IsothiocyanateHCID 597624006-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide2×

Product 1

HCID 597624191-Benzyl-N-(3,4-difluorobenzyl)-6-(4,5-dihydrothiazol-2-ylamino)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

General Procedure AA. To a solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide (Compound 172, 39 mg, 0.086 mmol) in CH2Cl2 (1 ml) was added 2-chloroethyl isothiocyanate (25 μl, 0.26 mmol) and Et3N (1 drop). The reaction was stirred at room temperature for 16 h and was purified directly by chromatography on silica gel (0→60% EtOAc-hexanes) to yield the title compound.

Workup

  1. customwas purified directly by chromatography on silica gel (0→60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4cef0ff173954a8dafb666fafb3a80f7
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

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