Methanol → HCID 9884133, compound

HRID 398421Notes

Reaction equation

HRID 398421 reaction equation
CO[C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C[O-].[Mg+2].C[O-].CO>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 53746175HCID 53746175, compound

Product 1

HCID 9884133HCID 9884133, compoundYield 35.1%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-chloro-phenyl)-3-cyclopentyl-propionic acid methyl ester (648 mg, 2.43 mmol) and 2-aminothiazole (487 mg, 4.86 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 14.0 mL, 9.72 mmol) was heated under reflux at 100° C. for 20 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 2-(4-chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (286 mg, 35%) as a white solid: mp 156.6-159.8° C.; EI-HRMS m/e calcd for C17H19ClN2OS (M+) 334.0906, found 334.0910.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-7ff8456ab3454af2b4c33d03462beb69
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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