2-Aminothiazole → HCID 30515126, compound

HRID 1162589Notes

Reaction equation

HRID 1162589 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C(N([CH:16]([CH3:18])[CH3:17])CC)(C)C.[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1>>[CH:6]([C:17]1[CH:16]=[CH:18][C:5]([C:23]2[N:24]=[C:20]([NH:19][C:7](=[O:9])[CH2:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[S:21][CH:22]=2)=[CH:4][CH:3]=1)([CH3:7])[CH3:2]

Participants

4

Reactant 3

HCID 21552-AminothiazoleHCID 159702-Thiopheneacetic acidHCID 81531Diisopropylethylamine

Product 1

HCID 30515126HCID 30515126, compoundYield 159.4%

Procedure

To the mixture of fluoro-N,N,N″,N″-tetramethylformamidinium hexafluorophosphate (TFFH) (290 mg, 1.1 mmol) and thiophen-2-acetic acid (156 mg, 1 mmol) at 0° C. was added diisopropylethylamine (0.35 mL, 2 mmol) and stirred at same temperature for 20 min. before adding 2-aminothiazole (261 mg, 1.2 mmol). The reaction mixture was warmed to room temperature and stirred for 12 h. The mixture was concentrated and loaded onto silica gel column to provide N-[4-(4-isopropyl-phenyl)-thiazol-2-yl]-2-thiophen-2-yl-acetamide (273 mg). LCMS m/z: 344 (M+1)+.

Workup

  1. stirringstirred for 12 h
  2. concentrationThe mixture was concentrated and loaded onto silica gel column

Sources & evidence

ORD record
ord-e1205a40b2344cf58b67ab033f49b170
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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