Diisopropylethylamine → HCID 23447599, compound

HRID 1840553Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][C:7]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:21])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Cl:31][C:32]1[CH:46]=[CH:45][C:35]2[C:36](=[O:44])[C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:38][O:39][C:34]=2[CH:33]=1>ClCCl>[C:1]([N:4]1[CH2:5][CH2:6][C:7]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:40]([C:37]3[C:36](=[O:44])[C:35]4[CH:45]=[CH:46][C:32]([Cl:31])=[CH:33][C:34]=4[O:39][CH:38]=3)(=[O:42])=[O:41])[CH2:17][C:16]2=[O:21])([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(1-acetyl-4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone (850 mg) and diisopropylethylamine (555 mg) in dichloromethane (15 ml) was gradually added dropwise at 0° C. a solution of 7-chloro-4-oxo-4H-benzopyran-3-sulfonyl chloride (960 mg) in dichloromethane (5 ml), and the mixture was stirred at 0° C. for 30 minutes. The reaction solution was diluted with dichloromethane, washed with water, citric acid solution, sodium bicarbonate solution and brine, dried and concentrated, and the residue was purified with silica gel column chromatography (ethyl acetate: methanol=10:1) to give pale yellow solid of 1-(1-acetyl-4-methoxycarbonylpiperidin-4-ylmethyl)-4-(7-chloro-4-oxo-4H-benzopyran-3-sulfonyl)-2-piperazinone (1.10 g).

Workup

washwashed with water, citric acid solution, sodium bicarbonate solution and brine
customdried
concentrationconcentrated
customthe residue was purified with silica gel column chromatography (ethyl acetate: methanol=10:1)

Sources & evidence

ORD record: ord-88bdcd174e5d4e42af8b7c5e0f82dd39
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680312B2

Reaction notes

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