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

HRID 362566Notes

Reaction equation

HRID 362566 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.C(N(CC)CC)C.[CH3:44][O:45][CH2:46][CH2:47][NH:48][CH2:49][CH2:50][O:51][CH3:52]>C1(C)C=CC=CC=1.ClCCl>[CH3:44][O:45][CH2:46][CH2:47][N:48]([CH2:49][CH2:50][O:51][CH3:52])[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

7

Reactant 4

HCID 2383Bis(2-Methoxyethyl)amineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 193536118-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid

Product 1

HCID 566253288-(4-Benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo [4,5-a]quinolizine-10-carboxylic acid bis-(2-methoxy-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

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

Sources & evidence

ORD record
ord-ef956bf103de48a49fe321845c94c494
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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