1,2-Dichloroethane → N-{1-[2-(5,7-Difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}-1-methyl-1H-1,2,3-benzotriazole-5-carboxamide

HRID 255345Notes

Reaction equation

HRID 255345 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[C:15]([F:21])[CH:16]=[C:17]([F:20])[CH:18]=3)[CH:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[CH3:23][N:24]1[C:28]2[CH:29]=[CH:30][C:31]([C:33](O)=[O:34])=[CH:32][C:27]=2[N:26]=[N:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[C:19]2[C:14]=1[CH:13]=[CH:12][C:11](=[O:22])[N:10]2[CH2:9][CH2:8][N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:33]([C:31]2[CH:30]=[CH:29][C:28]3[N:24]([CH3:23])[N:25]=[N:26][C:27]=3[CH:32]=2)=[O:34])[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27765491-methyl-1H-1,2,3-benzotriazole-5-carboxylic acidHCID 667740021-[2-(4-Amino-1-piperidinyl)ethyl]-5,7-difluoro-2(1H)-quinolinone2×

Product 1

HCID 15983193N-{1-[2-(5,7-Difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}-1-methyl-1H-1,2,3-benzotriazole-5-carboxamideYield 44.5%

Procedure

1-[2-(4-Aminopiperidin-1-yl)ethyl]-5,7-difluoroquinolin-2(1H)-one (Intermediate 23, 100 mg, 0.326 mmol) was reacted as described for Example 99 with 1-methyl-1H-1,2,3-benzotriazole-5-carboxylic acid (70 mg, 0.391 mmol), EDC (94 mg, 0.489 mmol) and HOBT (66 mg, 0.489 mol) to give title compound (67.6 mg).

Sources & evidence

ORD record
ord-18a6611767db4ffabcdbab4e9082303e
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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