Dimethylformamide → 8-(4-Benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid cyclopropylmethyl-(2-methoxy-ethyl)-amide

HRID 362557Notes

Reaction equation

HRID 362557 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:31])[N:17]3[C:22](=[C:23]([C:25]([OH:27])=O)[CH:24]=2)[C:21]2[S:28][CH:29]=[CH:30][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.[CH:41]1([CH2:44][NH:45][CH2:46][CH2:47][O:48][CH3:49])[CH2:43][CH2:42]1>C1(C)C=CC=CC=1.ClCCl.C(N(CC)CC)C>[CH:41]1([CH2:44][N:45]([CH2:46][CH2:47][O:48][CH3:49])[C:25]([C:23]2[CH:24]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][CH:11]=3)[C:16](=[O:31])[N:17]3[C:22]=2[C:21]2[S:28][CH:29]=[CH:30][C:20]=2[CH:19]=[CH:18]3)=[O:27])[CH2:43][CH2:42]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 193536298-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acidHCID 19353678(Cyclopropylmethyl)(2-methoxyethyl)amine

Product 1

HCID 566100038-(4-Benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid cyclopropylmethyl-(2-methoxy-ethyl)-amide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

From 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene. Then treatment with triethylamine and cyclopropylmethyl-(2-methoxy-ethyl)-amine in dichloromethane.

Sources & evidence

ORD record
ord-c122c191441844f687a82a7f23a2d44f
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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