Triethylamine → HCID 71811133, compound

HRID 1887917Notes

Reaction equation

HRID 1887917 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([F:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH:4]=1.C(N(CC)CC)C.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][N:31]=1>C(Cl)Cl.CN(C=O)C>[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:1][CH2:2][C:3]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][C:8]([F:14])=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[CH:4]=2)=[O:35])=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 71208513HCID 71208513, compound2×

Product 1

HCID 71811133HCID 71811133, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a mixture of 3-(aminomethyl)-7-fluoro-1-(2-fluorophenyl)quinolin-4(1H)-one (intermediate H) (470 mg, 1.64 mmol), triethylamine (0.229 mL, 1.64 mmol), and 35 mL of a CH2Cl2-DMF mixture was added 6-chloronicotinoyl chloride (298 mg, 1.64 mmol). The resulting mixture was stirred at room temperature for 1 hr. After this time, the reaction was complete, giving 6-chloro-N-[7-fluoro-1-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-3-yl-methyl]-nicotinamide (500 mg, 72%). MS calcd. for C22H14ClF2N3O2 [(M+H)+] 426.1, obsd. 426.1.

Sources & evidence

ORD record
ord-b98f0918d69e40b19c1b59ba0ad5a715
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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