Oxalyl chloride → 2-Chloro-N-(4-((4,4-difluorocyclohexyl)amino)quinazolin-8-yl)-5-(pivalamidomethyl)benzamide

HRID 1469809ノート

反応式

HRID 1469809 の反応式
[F:1][C:2]1([F:20])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH2:19])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:27][C:23]=1[C:24](O)=[O:25].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])=[CH:27][C:23]=1[C:24]([NH:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[NH:8][CH:5]1[CH2:6][CH2:7][C:2]([F:1])([F:20])[CH2:3][CH2:4]1)=[O:25]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 86692230N4-(4,4-difluorocyclohexyl)quinazoline-4,8-diamine

生成物 1

HCID 866922772-Chloro-N-(4-((4,4-difluorocyclohexyl)amino)quinazolin-8-yl)-5-(pivalamidomethyl)benzamide収率 21.9%

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-(4,4-difluorocyclohexyl)quinazoline-4,8-diamine (Intermediate-9, 60 mg, 0.215 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 116 mg, 0.431 mmol), oxalyl chloride (81 mg, 0.65 mmol), DMF (1 drop) and DIPEA (84 mg, 0.65 mmol) in CH2Cl2 (3 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.13 (s, 1H), 8.71 (d, 1H), 8.49 (s, 1H), 8.19 (m, 2H), 8.05 (d, 1H), 7.57-7.54 (m, 3H), 7.41 (d, 1H), 4.41 (m, 1H), 4.31 (d, 2H), 2.00 (m, 6H), 1.75 (m, 2H), 1.12 (s, 9H); MS (m/z): 530.20 (M+H)+.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-0d000e661d984affb9d5e963f35c1d2a
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

読み込み中…