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Acetic Anhydride → HCID 11375081, compound

HRID 1271070
Notes
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Reaction equation

HRID 1271070 reaction equation
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[Cl:15][C:16]1[CH:46]=[CH:45][C:19]([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([C:30](=[O:44])[C:31]([NH:33][C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[N:40]=[CH:39][CH:38]=[CH:37]4)=[O:32])=[CH:22]2)=[CH:18][CH:17]=1.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([C:30](=[O:44])[C:31]([N:33]([C:34]3[CH:35]=[C:36]4[C:41](=[CH:42][CH:43]=3)[N:40]=[CH:39][CH:38]=[CH:37]4)[C:12](=[O:14])[CH3:13])=[O:32])=[CH:22]2)=[CH:45][CH:46]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10203597Entasobulin

Product 1

HCID 11375081HCID 11375081, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

0.833 g (6.82 mMol) of DMAP, 1.38 g (13.6 mMol) of triethylamine and 13.9 g (136 mMol) of acetic anhydride are added, under nitrogen, to a stirred solution of 6.0 g (13.6 mMol) of 2-[1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-quinolin-6-ylacetamide in 60 ml of DMF. The reaction mixture is stirred at room temperature for 10 minutes and, after that, poured into 200 ml of ethyl acetate. After 300 ml of water have been added, the mixture is shaken in a separating funnel after which the two phase separate. Precipitation begins after 20 minutes. The pale yellow crystals are filtered off and dried in vacuo at 60° C.

Workup

  1. stirringthe mixture is shaken in a separating funnel after which the two phase
  2. customseparate
  3. customPrecipitation
  4. waitbegins after 20 minutes
  5. filtrationThe pale yellow crystals are filtered off
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-cd002fb98cc54947b11cb988e0813ee5
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07205299B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes