Triethylamine → HCID 71208220, compound

HRID 1887936Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][CH:10]=2)[N:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]=1[C:22]([O:24][CH3:25])=[O:23].[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:25][O:24][C:22]([C:4]1[N:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[C:11]([C:12](=[O:13])[C:3]=1[CH2:2][NH:1][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][CH:35]=[C:27]([Cl:26])[CH:28]=1)=[CH:10][CH:9]=[C:8]([O:14][CH3:15])[CH:7]=2)=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl 3-(aminomethyl)-7-methoxy-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (intermediate K) (30 mg, 0.089 mmol), 3-chlorobenzoyl chloride (35 mg, 0.200 mmol), and triethylamine (40 mg, 0.305 mmol) in methylene chloride (4 mL) was stirred at 0° C. for 1 hr. After this time, the reaction mixture was concentrated, and the crude material was triturated with diethyl ether. The product 3-[(3-chloro-benzoylamino)-methyl]-7-methoxy-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester was obtained without further purification. MS calcd. for C26H21ClN2O5 [(M+H)+] 477.1, obsd. 476.9.

Workup

concentrationAfter this time, the reaction mixture was concentrated
customthe crude material was triturated with diethyl ether

Sources & evidence

ORD record: ord-ed74c741d7ee40efbf2728130250d5ff
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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