Pyrrolidine → HCID 67442054, compound

HRID 1801379Notes

Reaction equation

HRID 1801379 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.Cl[S:16]([C:19]1[CH:20]=[C:21]([C:25]2[C:34]([CH3:36])([CH3:35])[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:37]([O:39][CH3:40])=[O:38])[CH:31]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17]>ClCCl>[CH3:35][C:34]1([CH3:36])[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:37]([O:39][CH3:40])=[O:38])[CH:31]=2)[N:26]=[C:25]1[C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([S:16]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:18])=[O:17])[CH:20]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 86658613HCID 86658613, compound

Product 1

HCID 67442054HCID 67442054, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of pyrrolidine (38 mg, 0.54 mmol) and N,N-diisopropylethylamine (116 mg, 0.90 mmol) in dichloromethane (4 mL) was added methyl 2-(3-(chlorosulfonyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (175 mg, 0.45 mmol) portionwise. The resultant yellow solution was stirred for 3 h at room temperature. The mixture was purified on preparative Thin layer chromatography to afford 163 mg of methyl 3,3-dimethyl-2-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-3,4-dihydroquinoline-6-carboxylate, which was used directly.

Workup

  1. customThe mixture was purified on preparative Thin layer chromatography

Sources & evidence

ORD record
ord-3b875a8a322b416b95206a93a3c1f55d
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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