Ammonium Hydroxide → HCID 49782491, compound

HRID 1923514Notes

Reaction equation

HRID 1923514 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][CH2:14][C:15]1[S:16][C:17]([C:20]([OH:22])=O)=[CH:18][N:19]=1.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][CH2:14][C:15]1[S:16][C:17]([C:20]([NH2:25])=[O:22])=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 66643592HCID 66643592, compound

Product 1

HCID 49782491HCID 49782491, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[2-(5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (73 mg, 0.23 mmol) in DMF (3 mL) was added 1,1′-carbonyldiimidazole (45 mg, 0.28 mmol). The resulting reaction mixture was stirred for 1 h at 60° C. and then treated with an ammonium hydroxide solution (357 μL, 2.3 mmol) and stirred overnight at room temperature. The reaction mixture was then evaporated. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) afforded the title compound (51 mg, 70%) as an off white solid. MS: m/e=315.0 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred overnight at room temperature
  3. customThe reaction mixture was then evaporated
  4. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-88c3b45ea40641a2abbb45ed2477ab1c
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…