Ammonia → HCID 68764955, compound

HRID 2391663Notes

Reaction equation

HRID 2391663 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]([C:19]3[S:23][C:22]([C:24]([O:26]C)=O)=[C:21]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])[CH:20]=3)[CH:17]=[N:18][C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:40]>CO>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]([C:19]3[S:23][C:22]([C:24]([NH2:40])=[O:26])=[C:21]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:37])([F:39])[F:38])[CH:20]=3)[CH:17]=[N:18][C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68767233HCID 68767233, compound

Product 1

HCID 68764955HCID 68764955, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.05 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B2a) and 100 ml of a saturated solution of ammonia in methanol was stirred in an autoclave at 120° C. for 3.5 h. The reaction mixture was allowed to cool down to room temperature, concentrated to dryness, dissolved in dichloromethane and filtered through a plug of silica gel (eluents: dichloromethane/ethyl acetate) to yield the title product.

Workup

  1. temperatureto cool down to room temperature
  2. concentrationconcentrated to dryness
  3. dissolutiondissolved in dichloromethane
  4. filtrationfiltered through a plug of silica gel (eluents: dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-4d6d2021265e4503bf5f34c9659f491a
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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