Oxalyl chloride → 6-Chloro-2-fluoro-3-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)benzamide

HRID 1469813노트

반응식

HRID 1469813 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[C:16]2[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1.[Cl:23][C:24]1[C:29]([C:30](O)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:26][CH:25]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:29]([C:30]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[CH:9][CH:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 716780474-(3-(Trifluoromethyl)phenoxy)quinolin-8-amine

생성물 1

HCID 716788876-Chloro-2-fluoro-3-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)benzamide수율 21.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinolin-8-amine (Intermediate-11, 100 mg, 0.327 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 200 mg, 0.699 mmol), oxalyl chloride (125 mg, 0.99 mmol), DMF (1 drop) and DIPEA (126 mg, 0.98 mmol) in CH2Cl2 (5 mL) to afford 40 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.79 (d, J=8.7 Hz, 1H), 8.73 (d, 1H), 8.17 (br t, 1H), 8.08 (d, J=8.7 Hz, 1H), 7.78-7.67 (m, 5H), 7.41-7.35 (m, 2H), 6.83 (d, 1H), 4.32 (d, 2H), 1.14 (s, 9H); MS [M+H]+: 574.31.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-9b90c222bb5d4bb0bfa13a607b43a2d8
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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