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Acetic Anhydride → 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

HRID 1681733
Notes
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Reaction equation

HRID 1681733 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]2[C:19](=[O:50])[CH:20]([CH:23]([OH:49])[C:24]3[N:25]=[CH:26][N:27]([C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:28]=3[CH3:29])[CH2:21][CH2:22][C:11]=12)[CH3:9]>N1C=CC=CC=1>[C:1]([O:49][CH:23]([C:24]1[N:25]=[CH:26][N:27]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:28]=1[CH3:29])[CH:20]1[C:19](=[O:50])[N:12]2[C:13]3[C:18]([C:10]([CH2:8][CH3:9])=[C:11]2[CH2:22][CH2:21]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1005366010-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 101002317-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2.0 ml) was added to a solution of 10-ethyl-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (2.15 g) in pyridine (10 ml). After being stirred at room temperature for 20 hours, the solution was evaporated in vacuo. The residue was dissolved in toluene (30 ml) and the solution was evaporated in vacuo to remove pyridine and acetic anhydride. This operation was repeated further three times to give 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one as an amorphous powder. This crude product was used in the next reaction without further purification.

Workup

  1. customthe solution was evaporated in vacuo
  2. dissolutionThe residue was dissolved in toluene (30 ml)
  3. customthe solution was evaporated in vacuo
  4. customto remove pyridine and acetic anhydride

Sources & evidence

ORD record
ord-91cdc543e5d147b18d8a0edc93150ff1
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05173493

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes