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Ammonia → 3-[1-(2-Chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thio-phene-2-carboxamide

HRID 2391579
Notes
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Reaction equation

HRID 2391579 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]1[CH:15]=[C:14]([N:16]2[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:19]=3[N:18]=[CH:17]2)[S:13][C:12]=1[C:25]([O:27]C)=O)[CH3:9].[NH3:29]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]1[CH:15]=[C:14]([N:16]2[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:19]=3[N:18]=[CH:17]2)[S:13][C:12]=1[C:25]([NH2:29])=[O:27])[CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 68771752methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 251530793-[1-(2-Chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thio-phene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
125 °C

Procedure

A mixture of 49 mg of the above-synthesized methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate and 5 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 5 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 yield 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-2f065faa948c4800af6b52b8f78d75cb
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