HCID 68783607, compound → HCID 46869492, compound

HRID 1519953Notes

Reaction equation

HRID 1519953 reaction equation
[O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:10]=[CH:9][S:8][C:7]=2[NH2:11])=[N:2]1.[F:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[F:23])[N:19]([CH2:24][C:25](O)=[O:26])[C:18](=[O:28])[CH:17]=[CH:16]2>>[O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:10]=[CH:9][S:8][C:7]=2[NH:11][C:25](=[O:26])[CH2:24][N:19]2[C:20]3[C:15](=[CH:14][C:13]([F:12])=[C:22]([F:23])[CH:21]=3)[CH:16]=[CH:17][C:18]2=[O:28])=[N:2]1

Participants

3

Reactant 2

HCID 68783607HCID 68783607, compoundHCID 68785144HCID 68785144, compound

Product 1

HCID 46869492HCID 46869492, compound

Procedure

The title compound was prepared from 3-(1,2,4-oxadiazol-3-yl)thiophen-2-amine (18 mg, 108 umol) and 2-(6,7-difluoro-2-oxoquinolin-1(2H)-yl)acetic acid (32 mg, 134 umol) using protocol A. The crude product was purified by HPLC to yield N-(3-(1,2,4-oxadiazol-3-yl)thiophen-2-yl)-2-(6,7-difluoro-2-oxoquinolin-1(2H)-yl)acetamide. Method [7] retention time 5.34 min by HPLC (M+=389) and (M+Na=411). 1H NMR (300 MHz, CDCl3) δ 11.06 (s, 1H), 8.69 (s, 1H), 7.74 (d, J=9.9 Hz, 1H), 7.42 (m, 2H), 7.35 (m, 1H), 6.98 (d, J=5.4 Hz, 1H), 6.86 (d, J=9.3 Hz, 1H), 5.22 (s, 2H).

Workup

  1. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-ea12d9703d1c429481f9c907c6c11a26
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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