Triethylamine → (3-{5-carbamoyl-4-[-1-(2-fluorophenyl)ethoxy]-2-thienyl}-3H-imidazo[4,5-c]pyridin-6-yl)methyl methanesulfonate

HRID 2391659Notes

Reaction equation

HRID 2391659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]1[CH:15]=[C:14]([N:16]2[C:20]3[CH:21]=[N:22][C:23]([CH2:25][OH:26])=[CH:24][C:19]=3[N:18]=[CH:17]2)[S:13][C:12]=1[C:27]([NH2:29])=[O:28])[CH3:9].[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(N(CC)CC)C>ClCCl>[CH3:30][S:31]([O:26][CH2:25][C:23]1[N:22]=[CH:21][C:20]2[N:16]([C:14]3[S:13][C:12]([C:27](=[O:28])[NH2:29])=[C:11]([O:10][CH:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[CH3:9])[CH:15]=3)[CH:17]=[N:18][C:19]=2[CH:24]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 687685763-[-1-(2-fluorophenyl)ethoxy]-5-[6-(hydroxymethyl)-3H-imidazo[4,5-c]pyridin-3-yl]thiophene-2-carboxamide

Product 1

HCID 86647119(3-{5-carbamoyl-4-[-1-(2-fluorophenyl)ethoxy]-2-thienyl}-3H-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), 2.9 g of 3-[-1-(2-fluorophenyl)ethoxy]-5-[6-(hydroxymethyl)-3H-imidazo[4,5-c]pyridin-3-yl]thiophene-2-carboxamide, 1.53 g of methanesulfonyl chloride, and 1.42 g of triethylamine in 70 ml dichloromethane give (3-{5-carbamoyl-4-[-1-(2-fluorophenyl)ethoxy]-2-thienyl}-3H-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-6e8ccb6e4ed04765959eaae3f62cacdd
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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