p-Toluenesulfonate → HCID 86650671, compound

HRID 1969472Notes

Reaction equation

HRID 1969472 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].[CH3:12][C:13]([NH:25][C@@H:26]1[CH2:30][C@H:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]([F:41])([F:40])[F:39])[CH:32]=2)[N:28]([C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=2)[C:27]1=[O:50])([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=1)[CH3:14]>ClCCl>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[CH3:14][C:13]([NH:25][C@@H:26]1[CH2:30][C@H:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]([F:41])([F:39])[F:40])[CH:32]=2)[N:28]([C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=2)[C:27]1=[O:50])([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[N:16]=1)[CH3:12]

Participants

4

Reactant 2

HCID 85570p-ToluenesulfonateHCID 44247662HCID 44247662, compound

Product 1

HCID 86650671HCID 86650671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tosylate Salt formation: Add p-toluenesulonic acid monohydrate (28.2 mg, 0.146 mmol) to a solution of 4-[(3R,5R)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-2-oxo-5-(3-trifluoromethoxy-phenyl)-pyrrolidin-1-yl]-benzonitrile (80 mg, 0.146 mmol) in dichloromethane. Evaporate to give a quantitative mass balance of 4-[(3R,5R)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-2-oxo-5-(3-trifluoromethoxy-phenyl)-pyrrolidin-1-yl]-benzonitrile tosylate as a foam. LC-MS ESI m/z: 548.6 (M+H)+, 571.6 (M+Na)+, Tr=2.34 min., method 2.

Workup

  1. customEvaporate

Sources & evidence

ORD record
ord-9f0ebb974bc8454a93886d153ac2ce86
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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