Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate → HCID 25107424, compound

HRID 604905Notes

Reaction equation

HRID 604905 reaction equation
Cl[CH:2]([C:8](=O)[C:9]([F:12])([F:11])[F:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:28][C:29]([NH2:31])=[S:30])[CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1>>[CH2:6]([O:5][C:3]([C:2]1[S:30][C:29]([NH:28][C:18]2[CH:19]=[CH:20][C:21]([N:22]3[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]3)=[C:16]([O:15][CH3:14])[CH:17]=2)=[N:31][C:8]=1[C:9]([F:12])([F:11])[F:10])=[O:4])[CH3:7]

Participants

3

Reactant 2

HCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoateHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 25107424HCID 25107424, compoundYield 24.2%

Procedure

The title compound was prepared in analogy to example 1 step e) from 76 mg (0.33 mmol) ethyl 2-chloro-3-keto-4,4,4-trifluorobutyrate and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The reaction was refluxed for 5 days. The crude product was purified on silica gel with methylene chloride/methanol 9/1. The crude product was stirred with methylene chloride/diethyl ether. The precipitate was filtered off and dried to yield 31 mg (24%) of 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester as a light yellow solid. MS ISP (m/e): 427.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=11.27 (s, 1H), 7.71 (s, 1H), 7.60 (s, 1H), 7.37 (d, 1H), 7.18 (d, 1H), 7.08 (d, 1H), 4.29 (q, 1H), 3.81 (s, 3H), 2.15 (s, 3H), 1.28 (t, 3H).

Workup

  1. temperatureThe reaction was refluxed for 5 days
  2. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-1281014f0dc545208b785ae9107b0f5c
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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