Oxalyl chloride → 2-Chloro-5-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)benzamide

HRID 1469808ノート

反応式

HRID 1469808 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[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:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)=[O:27]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 71680392N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

生成物 1

HCID 716787172-Chloro-5-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)benzamide収率 27.4%

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 N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-7, 50 mg, 0.164 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 88 mg, 0.326 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.24 (s, 1H), 10.16 (s, 1H), 8.83 (d, J=6.6 Hz, 1H), 8.69 (s, 1H), 8.33 (m, 2H), 8.23 (m, 2H), 7.75-7.55 (m, 4H), 7.50 (d, J=6.9 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 4.31 (d, J=5.4 Hz, 2H), 1.13 (s, 9H); MS [M+H]+: 556.23.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-521782071b2d495db3664833feb5cde5
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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