N-[5-(2-Bromoacetyl)-4-methyl-2-thiazolyl]acetamide → HCID 86649582, compound

HRID 2066798Notes

Reaction equation

HRID 2066798 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][C:6]=1[CH3:14])=O.[F:15][C:16]([F:24])([F:23])[C:17]1([C:20](=[S:22])[NH2:21])[CH2:19][CH2:18]1>CO.[OH-].[O-2].[P-3].[Mo]>[CH3:14][C:6]1[N:7]=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[S:9][C:5]=1[C:3]1[N:21]=[C:20]([C:17]2([C:16]([F:24])([F:23])[F:15])[CH2:19][CH2:18]2)[S:22][CH:2]=1

Participants

5

Reactant 2

HCID 19974111N-[5-(2-Bromoacetyl)-4-methyl-2-thiazolyl]acetamideHCID 86086574HCID 86086574, compound

Product 1

HCID 86649582HCID 86649582, compound

Reagents, catalysts & solvents 2

HCID 15935011104-88-4CatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[5-(2-bromo-acetyl)-4-methyl-thiazol-2-yl]-acetamide (0.29 g, prepared as described in WO 2005/068444) in MeOH (15 mL) at rt was added 1-trifluoromethyl-cyclopropanecarbothioic acid amide [871913-36-9] (0.20 g) and ammoniumphosphomolybdate (0.15 g). After stirring 18 h at rt, the reaction mixture was partitioned between EtOAc and water, the organic layers dried over Na2SO4 and evaporated to give the crude product. Purification by flash chromatography with an eluent of 1% MeOH in CH2Cl2 gave the title compound. MS (ESI): positive 348.1 (M+H), negative 346.1 (M−H).

Workup

  1. customthe reaction mixture was partitioned between EtOAc and water
  2. dry with materialthe organic layers dried over Na2SO4
  3. customevaporated
  4. customto give the crude product
  5. customPurification by flash chromatography with an eluent of 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-48ec6858d80f43d2ad9d095adb267fe5
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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