Diisopropyl Ether → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-cyclopropylaminocarbonyloxy-isoindolin-1-one

HRID 66334

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[N:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([N:16]3[CH:24]([O:25][C:26](OC4C=CC=CC=4)=[O:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:35])=[N:13]2)=[CH:8][CH:7]=1.C(OC(C)C)(C)C>C(#N)C>[Cl:5][C:6]1[N:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([N:16]3[CH:24]([O:25][C:26]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:35])=[N:13]2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Cyclopropylamine (2.85 g.) is added to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (4.3 g.) in acetonitrile (43 cc.), and the suspension obtained is stirred for 20 hours at a temperature of about 20° C. Diisopropyl ether (85 cc.) is then added, after which the insoluble product is filtered off and washed with diisopropyl ether (2 × 10 cc.). Recrystallisation from acetonitrile (130 cc.) gives 2-(7-chloro-1,8-naphthyridin-2-yl)-3-cyclopropylaminocarbonyloxy-isoindolin-1-one (3.2 g.) melting at 220° C.

Workup

customthe suspension obtained
filtrationafter which the insoluble product is filtered off
washwashed with diisopropyl ether (2 × 10 cc.)
customRecrystallisation from acetonitrile (130 cc.)

Sources & evidence

ORD record: ord-7bd64299fee340e4a2ee47755d6db096
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04131674

Linked notes

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