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
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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customthe solution was evaporated in vacuo
- dissolutionThe residue was dissolved in toluene (30 ml)
- customthe solution was evaporated in vacuo
- customto remove pyridine and acetic anhydride
Sources & evidence
- ORD record
- ord-91cdc543e5d147b18d8a0edc93150ff1
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05173493
Reaction notes
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