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

HRID 2391628Notes

Reaction equation

HRID 2391628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:11]2[CH:15]=[C:14]([N:16]3[C:24]4[CH:23]=[C:22]([CH2:25][OH:26])[N:21]=[CH:20][C:19]=4[N:18]=[CH:17]3)[S:13][C:12]=2[C:27]([NH2:29])=[O:28])[CH3:9])=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C>ClCCl>[CH3:34][S:35]([O:26][CH2:25][C:22]1[N:21]=[CH:20][C:19]2[N:18]=[CH:17][N:16]([C:14]3[S:13][C:12]([C:27](=[O:28])[NH2:29])=[C:11]([O:10][CH:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=4[C:30]([F:33])([F:31])[F:32])[CH3:9])[CH:15]=3)[C:24]=2[CH:23]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 687691013-{1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}-5-[6-(hydroxymethyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxamide

Product 1

HCID 86647110[1-(5-carbamoyl-4-{1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}-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), 120 mg of 3-{1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}-5-[6-(hydroxymethyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxamide, 57 mg of methanesulfonyl chloride, and 51 mg of triethylamine in 3 ml dichloromethane give [1-(5-carbamoyl-4-{1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}-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-b5f307bd3335469b86a8697259ffde3e
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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