Cyclohexanecarbonyl chloride → N-{3-Cyano-2-[(2-ethylbutanoyl)amino]-4,5,6,7-tetrahydro-1-benzothien-6-yl}-N-[1-(hydroxymethyl)-2,2-dimethylpropyl]cyclohexanecarboxamide

HRID 917350Notes

Reaction equation

HRID 917350 reaction equation
[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][CH:10]([NH:12][CH:13]([CH2:18][OH:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][C:6]=2[S:5][C:4]=1[NH:20][C:21](=[O:27])[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])#[N:2].C(N(C(C)C)CC)(C)C.[CH:37]1([C:43](Cl)=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>ClCCl>[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][CH:10]([N:12]([CH:13]([CH2:18][OH:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:43]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:44])[CH2:11][C:6]=2[S:5][C:4]=1[NH:20][C:21](=[O:27])[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])#[N:2]

Participants

5

Reactant 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 58962825N-(3-Cyano-6-{[1-(hydroxymethyl)-2,2-dimethylpropyl]amino}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Product 1

HCID 10028982N-{3-Cyano-2-[(2-ethylbutanoyl)amino]-4,5,6,7-tetrahydro-1-benzothien-6-yl}-N-[1-(hydroxymethyl)-2,2-dimethylpropyl]cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate isolated in Step A in 5.0 mL of dichloromethane was added 0.175 mL (1.00 mmol) of di-isopropylethylamine and 0.041 mL (0.280 mmol) of cyclohexanecarbonyl chloride. After stirring 16 h at ambient temperate, the reaction mixture was concentrated in vacuo, and purified by preparative reversed phase HPLC, affording the title compound as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-9fcd42c3b14d4dc2aecf5e63b8d6c034
Source dataset
uspto-grants-2007_09
Patent number
US07273876B2

Reaction notes

Loading…