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Ammonia → 5-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391615
Notes
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Reaction equation

HRID 2391615 reaction equation
CS(O[CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34](=[O:36])[NH2:35])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1)(=O)=O.[NH3:37]>CO>[NH2:37][CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34]([NH2:35])=[O:36])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:31])[F:32])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86647106[3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate

Product 1

HCID 687669945-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 150 mg of crude [3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate (example 49, step 1) in 5 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 80° C. for 1 h in the microwave cavity. The solvent is removed under reduced pressure. 20 ml of water and 20 ml dichloromethane is added to the residue, the organic phase is separated and the aqueous phase is extracted with 2×10 ml dichloromethane. The combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure. The resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)] to yield the title product.

Workup

  1. customThe solvent is removed under reduced pressure
  2. addition20 ml of water and 20 ml dichloromethane is added to the residue
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted with 2×10 ml dichloromethane
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)]

Sources & evidence

ORD record
ord-8c1d458b8d1648348a74b2705c079b7b
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