HCID 86601761, compound → HCID 178451099, compound

HRID 1162550Notes

Reaction equation

HRID 1162550 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)=O.[C:19]([O:23][C:24](=[O:36])[CH2:25][CH2:26][N:27]([CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[C:28]([NH2:30])=[S:29])([CH3:22])([CH3:21])[CH3:20]>CN1C(=O)CCC1>[C:19]([O:23][C:24](=[O:36])[CH2:25][CH2:26][N:27]([CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[C:28]1[S:29][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:7][CH:6]=2)[N:30]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 86601761HCID 86601761, compoundHCID 178461403HCID 178461403, compound

Product 1

HCID 178451099HCID 178451099, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The 2-bromo-1-[4-(trans-4-methyl-cyclohexyloxy)-phenyl]-ethanone (764 mg, 3.44 mmol), 3-(1-cyclopentyl-thioureido)-propionic acid tert-butyl ester (935 mg, 2.46 mmol), NMP (6 mL) were combined as indicated in general procedure B. The reaction was stirred at room temperature overnight. After an aqueous work up, the crude product was purified by silica gel chromatography (gradient, hexane→3% EtOAc-hexane) to afford 3-(cyclopentyl-{4-[4-(trans-4-methyl-cyclohexyloxy)-phenyl]-thiazol-2-yl}-amino)-propionic acid tert-butyl ester (1.05 g).

Workup

  1. customAfter an aqueous work up, the crude product was purified by silica gel chromatography (gradient, hexane→3% EtOAc-hexane)

Sources & evidence

ORD record
ord-eee50094ff82441c99f1d1c3d26c2c7b
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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