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

HRID 378686Notes

Reaction equation

HRID 378686 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:32])[N:17]3[C:22](=[C:23]([C:25](O)=[O:26])[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)C.[CH3:42][O:43][CH2:44][CH2:45][NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C1(C)C=CC=CC=1.ClCCl.C(N(CC)CC)C>[CH3:42][O:43][CH2:44][CH2:45][N:46]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:25]([C:23]1[CH:24]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=2)[C:16](=[O:32])[N:17]2[C:22]=1[C:21]1[N:28]=[CH:29][N:30]([CH3:31])[C:20]=1[CH:19]=[CH:18]2)=[O:26]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1581105N-(2-methoxyethyl)anilineHCID 193536118-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid

Product 1

HCID 566216068-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]-quinolizine-10-carboxylic acid (2-methoxy-ethyl)-phenyl-amide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 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)-phenyl-amine in dichloromethane.

Sources & evidence

ORD record
ord-c2e2b4ddbd61415a875a0e87b5addbf3
Source dataset
uspto-grants-2000_02
Patent number
US06030984

Reaction notes

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