Sodium hydride → 2-({Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-methyl)-benzoic acid

HRID 1162557Notes

Reaction equation

HRID 1162557 reaction equation
[CH:1]1([NH:6][C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30]Br.[H-].[Na+]>>[CH:1]1([N:6]([CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([OH:32])=[O:22])[C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=3)[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 86079884Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amine

Product 1

HCID 115390282-({Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-methyl)-benzoic acidYield 16.1%

Procedure

2-({Cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-methyl)-benzoic acid (19 mg) was prepared following general method S2 using cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amine (80 mg, 0.28 mmol), 2-bromomethyl-benzoic acid methyl ester (68 mg, 0.33 mmol) and NaH (34 mg, 60%, 0.84 mmol). Purification (Silica gel, ethyl acetate/hexane 5:95) provided the ester, which was hydrolyzed following general procedure T. Sodium 2-({cyclopentyl-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-amino}-methyl)-benzoate was prepared following procedure J. LCMS m/z: 422 (M+1)+.

Workup

  1. customPurification (Silica gel, ethyl acetate/hexane 5:95)

Sources & evidence

ORD record
ord-06ff8cbeb88c46b6b53138c589cdcc39
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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