Water → 2-(5-Chloropyrid-2-yl)-3-(4-ethoxycarbonylpiperazin-1-yl)carbonyloxy-isoindolin-1-one

HRID 27081Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:23]([O:24]C(OC3C=CC=CC=3)=O)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:34])=[N:13][CH:14]=1.Cl.[CH2:36]([O:38][C:39]([N:41]1CCNCC1)=[O:40])[CH3:37].[OH2:47]>C(#N)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:23]([O:24][C:1]([N:3]3[CH2:6][CH2:7][N:41]([C:39]([O:38][CH2:36][CH3:37])=[O:40])[CH2:5][CH2:4]3)=[O:47])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:34])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Triethylamine (3.03 g.) is added to a suspension of 2-(5-chloropyrid-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (3.8 g.) and 1-ethoxycarbonylpiperazine hydrochloride (4.86 g.) in acetonitrile (50 cc.), and the mixture is stirred for 18 hours at a temperature of about 20° C. Water (100 cc.) is then added and the insoluble product is filtered off and washed with water (10 cc.). After drying, a product (4 g.) is obtained which, after recrystallisation from acetonitrile (30 cc.), gives 2-(5-chloropyrid-2-yl)-3-(4-ethoxycarbonylpiperazin-1-yl)carbonyloxy-isoindolin-1-one (2.8 g.) melting at 160° C.

Workup

filtrationthe insoluble product is filtered off
washwashed with water (10 cc.)
customAfter drying
customa product (4 g.) is obtained which
customafter recrystallisation from acetonitrile (30 cc.)

Sources & evidence

ORD record: ord-5f6592c6a4384358a914cfdad510b3b6
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220646

Reaction notes

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