Methanol → HCID 22467915, compound

HRID 1935239Notes

Reaction equation

HRID 1935239 reaction equation
C([O:3][C:4](=O)[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[NH2:27][C:28]1[S:29][CH:30]=[CH:31][N:32]=1.C[O-].[Mg+2].C[O-].CO>>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([C:21]3[NH:22][CH:23]=[CH:24][N:25]=3)(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:4]([NH:27][C:28]2[S:29][CH:30]=[CH:31][N:32]=2)=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 67485030HCID 67485030, compound

Product 1

HCID 22467915HCID 22467915, compoundYield 19.1%

Conditions

Temperature
110 °C

Procedure

A mixture of 3-cyclopentyl-2-[4-(1H-imidazole-2-sulfonyl)-phenyl]-propionic acid ethyl ester (113.5 mg, 0.30 mmol) and 2-aminothiazole (45.3 mg, 0.45 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. %, 0.86 mL, 0.60 mmol) was heated at 110° C. for 8 h. At this time, the reaction was cooled to 25° C., filtered through a plug of celite, and washed with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded the 3-cyclopentyl-2-[4-(1H-imidazole-2-sulfonyl)-phenyl]-N-thiazol-2-yl-propionamide (24.7 mg, 19%) as a tan solid: mp 249-251° C.; EI-HRMS m/e calcd for C20H22N4O2S2 (M+) 430.1133 found 430.1133.

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. filtrationfiltered through a plug of celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-38310c2067264adb83acb0b66b5c37cd
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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