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

HRID 1644475Notes

Reaction equation

HRID 1644475 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][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=2)[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](=[O:34])[C:32]2[CH:31]=[CH:30][C:29]([C:26]3[N:25]=[C:24]([CH3:23])[O:28][N:27]=3)=[CH:37][CH:36]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 71278084-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acidHCID 667740021-[2-(4-Amino-1-piperidinyl)ethyl]-5,7-difluoro-2(1H)-quinolinone2×

Product 1

HCID 66774883N-{1-[2-(5,7-Difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzamideYield 44.7%

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 4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid (80 mg, 0.391 mmol), EDC (94 mg, 0.489 mmol) and HOBT (66 mg, 0.489 mmol). Solvent removed and the obtained solids were suspended in ethyl acetate and then filtered to give title compound (71.9 mg).

Workup

  1. customSolvent removed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-892e4966a5fe48db92ee56a451eccc97
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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