Ammonia → HCID 25153286, compound

HRID 2391589Notes

Reaction equation

HRID 2391589 reaction equation
[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17]C)=O)=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH:11]=2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.[NH3:31]>CO>[N:1]1([C:10]2[S:14][C:13]([C:15]([NH2:31])=[O:17])=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:29])([F:28])[F:30])[CH:11]=2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68766387HCID 68766387, compound

Product 1

HCID 25153286HCID 25153286, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2.50 g of methyl 5-(1H-imidazo[4,5-b]pyridin-1-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B5a) and 250 ml of a saturated solution of ammonia in methanol was stirred in an autoclave at 130° C. for 12 h. The reaction mixture was allowed to cool down to room temperature, concentrated, and the resulting residue was purified by flash chromatography (neutral alumina oxide, eluents: ethyl acetate/methanol). After crystallization from acetonitrile the title compound was obtained.

Workup

  1. temperatureto cool down to room temperature
  2. concentrationconcentrated
  3. customthe resulting residue was purified by flash chromatography (neutral alumina oxide, eluents: ethyl acetate/methanol)
  4. customAfter crystallization from acetonitrile the title compound
  5. customwas obtained

Sources & evidence

ORD record
ord-363d2b91651448e0b97c949136019a47
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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