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Sec-Butylamine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-sec-butylaminocarbonyloxy-isoindolin-1-one

HRID 66333
Notes
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Reaction equation

HRID 66333 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22](OC4C=CC=CC=4)=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:4][CH:3]=1.[CH:32]([NH2:36])([CH2:34][CH3:35])[CH3:33]>C(OC(C)C)(C)C>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([NH:36][CH:32]([CH2:34][CH3:35])[CH3:33])=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 233436372-(7-Chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-1-isoindolinone

Product 1

HCID 227547382-(7-Chloro-1,8-naphthyridin-2-yl)-3-sec-butylaminocarbonyloxy-isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-phenoxycarbonyloxy-isoindolin-1-one (8.6 g.) and sec-butylamine (40 cc.) is heated at 65° C. until dissolution. The reaction mixture is then diluted with diisopropyl ether (240 cc.). The precipitate formed is filtered off and recrystallised from acetonitrile (60 cc.). 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-sec-butylaminocarbonyloxy-isoindolin-1-one (3 g.), melting at 220°-222° C., is thus obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. customrecrystallised from acetonitrile (60 cc.)

Sources & evidence

ORD record
ord-023d2509928949a9bbadc17115bc650a
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04131674

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes