Triethylamine → (1-{5-carbamoyl-4-[1-(2-chlorophenyl)-2,2,2-trifluoroethoxy]-2-thienyl}-1H-imidazo[4,5-c]pyridin-6-yl)methyl methanesulfonate

HRID 2391625Notes

Reaction equation

HRID 2391625 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:13][C:14]1[CH:18]=[C:17]([N:19]2[C:27]3[CH:26]=[C:25]([CH2:28][OH:29])[N:24]=[CH:23][C:22]=3[N:21]=[CH:20]2)[S:16][C:15]=1[C:30]([NH2:32])=[O:31])[C:9]([F:12])([F:11])[F:10].[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>ClCCl>[CH3:33][S:34]([O:29][CH2:28][C:25]1[N:24]=[CH:23][C:22]2[N:21]=[CH:20][N:19]([C:17]3[S:16][C:15]([C:30](=[O:31])[NH2:32])=[C:14]([O:13][CH:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:9]([F:12])([F:11])[F:10])[CH:18]=3)[C:27]=2[CH:26]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68766267HCID 68766267, compound

Product 1

HCID 86647108(1-{5-carbamoyl-4-[1-(2-chlorophenyl)-2,2,2-trifluoroethoxy]-2-thienyl}-1H-imidazo[4,5-c]pyridin-6-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described for example 49 (step 1), 170 mg of 3-[1-(2-chlorophenyl)-2,2,2-trifluoroethoxy]-5-[6-(hydroxymethyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxamide, 76.7 mg of methanesulfonyl chloride, and 70.8 mg of triethylamine in 3 ml dichloromethane give (1-{5-carbamoyl-4-[1-(2-chlorophenyl)-2,2,2-trifluoroethoxy]-2-thienyl}-1H-imidazo[4,5-c]pyridin-6-yl)methyl methanesulfonate as crude material that is used for step 2 without further purification.

Sources & evidence

ORD record
ord-3ea488ce27c94e87adc046cbd3d12d2c
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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