Toluene → 8-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo [4,5-a]-quinolizine-10-carboxylic acid (2-methoxy-ethyl)-propyl-amide

HRID 378689Notes

Reaction equation

HRID 378689 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:32])[N:17]3C(=C(C(O)=O)[CH:24]=2)[C:21]2[N:28]=[CH:29][N:30]([CH3:31])[C:20]=2[CH:19]=[CH:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.CN(C=[O:41])C.[CH3:42][O:43][CH2:44][CH2:45][NH:46][CH2:47][CH2:48][CH3:49].[C:50]1([CH3:56])C=CC=C[CH:51]=1>ClCCl.C(N(CC)CC)C>[CH3:42][O:43][CH2:44][CH2:45][N:46]([CH2:51][CH2:50][CH3:56])[C:47]([C:48]1[CH:24]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[C:16](=[O:32])[N:17]2[C:49]=1[C:21]1[N:28]=[CH:29][N:30]([CH3:31])[C:20]=1[CH:19]=[CH:18]2)=[O:41]

Participants

8

Reactant 5

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 12238049N-(2-Methoxyethyl)propylamineHCID 193536118-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid

Product 1

HCID 566237668-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo [4,5-a]-quinolizine-10-carboxylic acid (2-methoxy-ethyl)-propyl-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-propyl-amine in dichloromethane.

Sources & evidence

ORD record
ord-5a43d07d497c4d6a91b438171d29bb7e
Source dataset
uspto-grants-2000_02
Patent number
US06030984

Reaction notes

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