Oxalyl chloride → 3-Chloro-6-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)picolinamide

HRID 1469801노트

반응식

HRID 1469801 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[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[CH:10]=[CH:9][N:8]=1.[Cl:23][C:24]1[C:25]([C:38](O)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:29]=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:25]([C:38]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[CH:10]=[CH:9][N: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:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:28][CH:29]=1

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 716780491-(3-(Trifluoromethyl)phenoxy)isoquinolin-5-amineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

생성물 1

HCID 716785453-Chloro-6-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)picolinamide수율 10.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using 1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-amine (Intermediate-6, 100 mg, 0.329 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 126 mg, 0.46 mmol), oxalyl chloride (87 mg, 0.69 mmol), DMF (1 drop) and DIPEA (129 mg, 1.00 mmol) in CH2Cl2 (5 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.89 (s, 1H), 8.34-8.30 (m, 2H), 8.17 (d, J=7.5 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H), 8.00 (d, J=6.3 Hz, 1H), 7.83-7.78 (t, J=7.8 Hz, 1H), 7.73-7.67 (m, 5H), 7.40 (d, J=8.7 Hz, 1H), 4.45 (d, J=6.0 Hz, 2H), 1.17 (s, 9H); MS [M+H]+: 557.18.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-5e337ce6274b43db963b511be4b3545d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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