Diisopropylethylamine → HCID 23447599, compound

HRID 2186141Notes

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-d4e1b4fa18734a83886e6b8e2d5d98fe
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403595B1

Reaction notes

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