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

HRID 1469812ノート

反応式

HRID 1469812 の反応式
[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: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[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: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

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 716780474-(3-(Trifluoromethyl)phenoxy)quinolin-8-amineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

生成物 1

HCID 866922793-Chloro-6-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)picolinamide収率 38.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

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), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 180 mg, 0.66 mmol), oxalyl chloride (125 mg, 0.99 mmol), DMF (1 drop) and DIPEA (126 mg, 0.98 mmol) in CH2Cl2 (5 mL) to afford 70 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.86 (s, 1H), 8.91 (d, J=6.9 Hz, 1H), 8.81 (d, 1H), 8.35 (br t, 1H), 8.12 (d, J=7.8 Hz, 1H), 8.06 (d, J=9.1 Hz, 1H), 7.80-7.70 (m, 5H), 7.47 (d, J=7.8 Hz, 1H), 6.83 (d, J=4.8 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H), 1.16 (s, 9H); MS [M+H]+: 557.26.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-e8dc5cb8e4f540219d4e84a5587e6aed
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

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