Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinamide

HRID 1469861ノート

反応式

HRID 1469861 の反応式
[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH2:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][CH:18]([F:35])[C:19]1[N:27]=[CH:26][C:25]([CH2:28][NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])=[CH:24][C:20]=1[C:21](O)=[O:22].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:21](=[O:22])[C:20]3[CH:24]=[C:25]([CH2:28][NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH:26]=[N:27][C:19]=3[CH:18]([F:35])[F:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 710598402-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

生成物 1

HCID 71680227N-(4-(tert-Butylamino)quinazolin-8-yl)-2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinamide収率 5.5%

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-(tert-butyl)quinazoline-4,8-diamine (Intermediate-55, 100 mg, 0.46 mmol), 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid (Intermediate-66, 150 mg, 0.55 mmol), oxalyl chloride (104 mg, 0.83 mmol), DMF (1 drop) and DIPEA (178 mg, 1.38 mmol) in CH2Cl2 (2 mL) to afford 12 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.32 (s, 1H), 8.71 (s, 1H), 8.63 (m, 1H), 8.49 (m, 2H), 8.16 (d, 1H), 8.05 (m, 1H), 7.46 (m, 2H), 7.22 (t, J=54 Hz, 1H), 4.42 (d, 2H), 1.55 (s, 9H), 1.05 (d, J=6.6 Hz, 6H); MS [M+H]+: 471.49.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-67a9824fdbb94d6d9a27913abd2d1066
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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