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Acetic Anhydride → 5-Acetyl-2-chloro-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2380265
Notes
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Reaction equation

HRID 2380265 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:21])[C:5]2[NH:6][C:7](=[O:20])[C:8]3[CH:19]=[CH:18][CH:17]=[N:16][C:9]=3[N:10]([CH:13]3[CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C)C1C=CN=CC=1>[C:22]([N:6]1[C:7](=[O:20])[C:8]2[CH:19]=[CH:18][CH:17]=[N:16][C:9]=2[N:10]([CH:13]2[CH2:15][CH2:14]2)[C:11]2[N:12]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:21])[C:5]1=2)(=[O:24])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 463143Dipyridodiazepinone deriv. 14

Product 1

HCID 199600305-Acetyl-2-chloro-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloro-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one and acetic anhydride with 4-dimethylaminopyridine was heated at 130° C. until a clear solution was obtained. The solvent was evaporated and the residue was chromatographed over silica gel with ethyl acetate/hexane to give 0.85 g of the title compound, which crystallized from isopropyl ether/ethyl acetate, m.p. 204°-206° C.

Workup

  1. customwas obtained
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1c776c15f84549e2a2bf28b39cf8ccb4
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05366972

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes