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Ammonia → 5-(1H-Imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391583
Notes
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Reaction equation

HRID 2391583 reaction equation
[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17]C)=O)=[C:12]([O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:30])[F:29])[CH3:21])[CH:11]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[NH3:32]>CO>[N:1]1([C:10]2[S:14][C:13]([C:15]([NH2:32])=[O:17])=[C:12]([O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:29])([F:30])[F:31])[CH3:21])[CH:11]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 68767622methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoro-methyl)phenyl]ethoxy}thiophene-2-carboxylate

Product 1

HCID 251530815-(1H-Imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
125 °C

Procedure

A mixture of 86 mg of the above-synthesized methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate and 10 ml of a saturated solution of ammonia in methanol was stirred in a microwave vial at 125° C. for 4 h in the microwave cavity. The reaction mixture was allowed to cool down to room temperature, then another 10 ml of a saturated solution of ammonia in methanol were added and the procedure was repeated as described above. The solvent was removed under vacuum and the residue was purified by flash chromatography to give the title compound.

Workup

  1. temperatureto cool down to room temperature
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-08343b308db54eeab35642105a7e11d1
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273890B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes