Methanesulfonyl chloride → HCID 18771474, compound

HRID 1992192Notes

Reaction equation

HRID 1992192 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:13][S:14]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 571728Methyl 4-(aminomethyl)benzoate

Product 1

HCID 18771474HCID 18771474, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure outlined in scheme example 929, starting from 4-(aminomethyl)benzoic acid (2.00 g, 13.24 mmol) was treated with sulfuric acid to form methyl 4-(aminomethyl)benzoate (1.20 g, 55%). Methyl 4-(aminomethyl)benzoate (0.600 g, 3.63 mmol) was treated with methanesulfonyl chloride (0.832 g, 7.26 mmol)) in DCM (20 ml) to give crude methyl 4-{[(methylsulfonyl)amino]methyl}benzoate (0.398 g, 45%). Methyl 4-{[(methylsulfonyl)amino]methyl}benzoate (0.398 g, 1.63 mmol) was treated with NaOH and methanol to give 4-{[(methylsulfonyl)amino]methyl}benzoic acid hydrochloride (0.370 g, 98%). The title compound, N-({4-[(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-1-piperidinyl)carbonyl]phenyl}methyl) methanesulfonamide (0.128 g, 50%) was obtained as a oil from 4-{[(methylsulfonyl)amino]methyl}benzoic acid hydrochloride (0.132 g, 0.461), 1-(8-{2-[4-(3-Fluoro-phenyl)-piperidin-4-yl]-ethyl}-8-aza-bicyclo[3.2.1]oct-3-yl)-2-methyl-1H-enzoimidazole dihydrochloride (0.200 g, 0.39 mmol) and HATU (0.150 g, 0.46 mmol) following the procedure outlined in example 5. ES-LCMS m/z 658 (M+1).

Sources & evidence

ORD record
ord-117c0bf8e93b4c5aa6cad75c5a0eec9a
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…