Oxalyl chloride → 3-Chloro-6-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)picolinamide

HRID 1469803ノート

反応式

HRID 1469803 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][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:20][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[N:13]=[CH:12][N:11]=[C:10]3[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[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 71680392N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

生成物 1

HCID 716787143-Chloro-6-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)picolinamide収率 43.8%

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 N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-7, 50 mg, 0.164 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 85 mg, 0.314 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 40 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 11.62 (s, 1H), 10.14 (s, 1H), 8.94 (d, J=7.8 Hz, 1H), 8.77 (s, 1H), 8.32-8.27 (m, 4H), 8.11 (d, J=8.7 Hz, 1H), 7.75-7.64 (m, 2H), 7.51-7.46 (m, 2H), 4.49 (d, J=5.7 Hz, 2H), 1.17 (s, 9H); MS [M+H]+: 557.16.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-8d8e84f950d24ddb9c0e7ef08c301774
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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