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

HRID 2391639Notes

Reaction equation

HRID 2391639 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.[CH3:37][NH2:38]>CO>[CH3:37][NH:38][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:32])([F:33])[F:31])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 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 687717665-{6-[(methylamino)methyl]3H-imidazo[4,5-c]pyridin-3-yl}-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 75 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) and 0.32 ml methylamine (2 M solution in methanol) in 1.5 ml methanol is stirred in a microwave vial at 120° C. for 6 h in the microwave cavity. The reaction mixture is concentrated to dryness and the resulting residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v)) to obtain the title product.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe resulting residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v))

Sources & evidence

ORD record
ord-b8c9bc1145b14714ae71bef185d03189
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

Loading…