N-methyl-2-pyrrolidone → HCID 21192602, compound

HRID 1068010Notes

Reaction equation

HRID 1068010 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:20]Cl)[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.[NH:35]1[CH2:38][CH:37]([OH:39])[CH2:36]1.CN1C(=[O:46])CCC1>ClCCl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:46])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][N:35]4[CH2:38][CH:37]([OH:39])[CH2:36]4)[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 21192607HCID 21192607, compound

Product 1

HCID 21192602HCID 21192602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-1,4-dihydro-3-quinolinecarboxamide (0.09 gm) from Preparation No. 35 in dry NMP (2 mL) containing diisopropylethylamine (0.14 mL) is treated with 3-azetidinol hydrochloride (0.04 gm) (prepared as described in Helv. Chim. Acta 1988, 1035). The reaction mixture is stirred overnight. The reaction mixture is diluted with dichloromethane (50 mL) and washed with water (2×10 mL), brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue is purified by flash column chromatography eluting with 5% to 20% methanol in dichloromethane and then by recrystallization from methanol-acetonitrile to afford 0.08 gm of the title compound as an off-white solid.

Workup

  1. washwashed with water (2×10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash column chromatography
  5. washeluting with 5% to 20% methanol in dichloromethane
  6. customby recrystallization from methanol-acetonitrile

Sources & evidence

ORD record
ord-27916440698b4af0999dfe69e61ff75f
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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