Diisopropylethylamine → HCID 67442632, compound

HRID 1801384Notes

Reaction equation

HRID 1801384 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3]1.C(N(CC)C(C)C)(C)C.Cl[S:18]([C:21]1[CH:22]=[C:23]([C:27]2[C:36]([CH3:38])([CH3:37])[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:39]([O:41][CH3:42])=[O:40])[CH:33]=3)[N:28]=2)[CH:24]=[CH:25][CH:26]=1)(=[O:20])=[O:19]>ClCCl>[CH3:37][C:36]1([CH3:38])[CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:39]([O:41][CH3:42])=[O:40])[CH:33]=2)[N:28]=[C:27]1[C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([S:18](=[O:20])(=[O:19])[NH:7][CH:4]2[CH2:5][CH2:6][N:2]([CH3:1])[CH2:3]2)[CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 189403961-Methylpyrrolidin-3-amineHCID 86658613HCID 86658613, compound

Product 1

HCID 67442632HCID 67442632, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-methylpyrrolidin-3-amine (52 mg, 0.52 mmol) and N,N-diisopropylethylamine (112 mg, 0.86 mmol) in dichloromethane (4 mL) was added methyl 2-(3-(chlorosulfonyl)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (170 mg, 0.43 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 152 mg of methyl 3,3-dimethyl-2-(3-(N-(1-methylpyrrolidin-3-yl)sulfamoyl)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-d684c25438fe47b1b0eb7f6bcf6399af
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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