Oxalyl chloride → 2-Chloro-5-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)benzamide

HRID 1469811노트

반응식

HRID 1469811 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[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:29][C:25]=1[C:26](O)=[O:27].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[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:29][C:25]=1[C:26]([NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)=[O:27]

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 716780474-(3-(Trifluoromethyl)phenoxy)quinolin-8-amine

생성물 1

HCID 716788862-Chloro-5-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)benzamide수율 20.4%

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, 40 mg, 0.132 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 200 mg, 0.743 mmol), oxalyl chloride (140 mg, 1.11 mmol), DMF (1 drop) and DIPEA (52 mg, 0.40 mmol) in CH2Cl2 (5 mL) to afford 15 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.5 (s, 1H), 9.01 (d, J=7.8 Hz, 1H), 8.60 (d, J=4.8 Hz, 1H), 8.05 (d, J=8.7 Hz, 1H), 7.71-7.60 (m, 4H), 7.48-7.38 (m, 4H), 6.64 (d, J=5.1 Hz, 1H), 6.05 (br s, 1H), 4.49 (d, J=6.0 Hz, 2H), 1.23 (s, 9H); MS [M+H]+: 556.19.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-0c5480dfa9fe4e4cbc91a1b2af550cbb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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