2-Aminothiazole → HCID 23394567, compound

HRID 398659Notes

Reaction equation

[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][O:21][CH3:22])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:50][C:51]1[S:52][CH:53]=[CH:54][N:55]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][O:21][CH3:22])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([NH:50][C:51]2[S:52][CH:53]=[CH:54][N:55]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methoxymethanesulfonyl-phenyl)-propionic acid (31 mg, 0.09 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (67 mg, 0.15 mmol), and 2-aminothiazole (15 mg, 0.15 mmol) in methylene chloride (1 mL) at 25° C. was treated with triethylamine (0.04 mL, 0.29 mmol). The reaction was stirred at 25° C. for 20 h. At this time, the reaction was treated with a saturated aqueous sodium bicarbonate solution. The resulting organic layer was washed with a 1N aqueous hydrochloric acid solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methoxymethanesulfonyl-phenyl)-N-thiazol-2-yl-propionamide (23 mg, 59.2%) as a white solid: mp 157-160° C.; EI-HRMS m/e calcd for C19H24N2O4S2 (M+) 408.1178, found 408.1178.

Workup

washThe resulting organic layer was washed with a 1N aqueous hydrochloric acid solution
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-54ccd66dc5ac435fb6280cc575c8ab34
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610846B1

Reaction notes

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