Ammonium Hydroxide → 2-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid amide

HRID 1923587Notes

Reaction equation

HRID 1923587 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:20](O)=[O:21])=[CH:18][N:19]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[N:6][CH:7]=1.C(N1C=CN=C1)([N:26]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:20]([NH2:26])=[O:21])=[CH:18][N:19]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 666436102-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid

Product 1

HCID 595685332-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid amideYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid (83 mg, 0.25 mmol) in DMF (2.5 mL) was added 1,1′-carbonyldiimidazole (49 mg, 0.3 mmol). The resulting reaction mixture was stirred for 1 h at 60° C. and then treated with an ammonium hydroxide solution (25%, 385 μL, 2.5 mmol) and stirred for 2 h at room temperature. The reaction mixture was then evaporated. Purification by trituration from water/methanol afforded the title compound (64 mg, 77%) as an off white solid after. MS: m/e=331.0 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 2 h at room temperature
  3. customThe reaction mixture was then evaporated
  4. customPurification by trituration from water/methanol

Sources & evidence

ORD record
ord-0b046c6520e045a99aa66b597387f181
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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