Water → HCID 86603039, compound

HRID 855285Notes

Reaction equation

HRID 855285 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([CH3:13])[N:12]=1)=[O:4].[H-].[Na+].[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:5]([CH2:6][CH2:7][C:8]2[S:9][CH:10]=[C:11]([CH3:13])[N:12]=2)[C:3](=[O:4])[C:2]([F:14])([F:1])[F:15])=[CH:28][CH:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 39072071HCID 39072071, compound

Product 1

HCID 86603039HCID 86603039, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 224 mg of 2,2,2-trifluoro-N-[2-(4-methyl-thiazol-2-yl)-ethyl]-acetamide (0.94 mmol) in 4 ml DMF was added to a suspension of 45 mg of sodium hydride (60% in mineral oil) in 4 ml DMF at 0° C. After 30 min 0.173 ml 4-tert-butyl-benzylbromide were added and the reaction mixture was allowed to warm to rt. Stirring was continued for 3 h at ambient temperature, then water was added and the mixture was extracted with EtOAc. The organic layers were dried over magnesium sulfate, filtrated and the solvent was evaporated. Chromatography (silica gel; cyclohexane/EtOAc 4:1) yielded 265 mg (73%) of N-(4-tert-butyl-benzyl)-2,2,2-trifluoro-N-[2-(4-methyl-thiazol-2-yl)-ethyl]-acetamide as a light yellow liquid. 1H NMR (CDCl3, 300 MHz): δ 1.30 (s) and 1.31 (s, 9H), 2.42 (s, 3H), 3.23 (q, J=7 Hz, 2H), 3.70 (t, J=7 Hz) and 3.79 (t, J=7 Hz, 2H), 4.48(s) and 4.62 (s, 2H), 6.77 (m, 1H), 7.10 (d, J=8 Hz) and 7.17 (d, J=8 Hz, 2H), 7.36 (d, J=8 Hz) and 7.38 (d, J=8 Hz, 2H); MS (ISP) 385.4 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. filtrationfiltrated
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e5f5193120b34494b1179071c78de6cc
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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