Oxalyl chloride → 2-(Difluoromethyl)-5-(isobutyramidomethyl)-N-(4-(isopropylamino)quinazolin-8-yl)nicotinamide

HRID 1469862ノート

反応式

HRID 1469862 の反応式
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].[F:16][CH:17]([F:34])[C:18]1[N:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])=[CH:23][C:19]=1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[F:34][CH:17]([F:16])[C:18]1[N:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:33])[CH:30]([CH3:31])[CH3:32])=[CH:23][C:19]=1[C:20]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][N:6]=[C:5]2[NH:4][CH:1]([CH3:3])[CH3:2])=[O:21]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 710598402-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acidHCID 86692303N4-isopropylquinazoline-4,8-diamine

生成物 1

HCID 716802282-(Difluoromethyl)-5-(isobutyramidomethyl)-N-(4-(isopropylamino)quinazolin-8-yl)nicotinamide収率 4.4%

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-isopropylquinazoline-4,8-diamine (Intermediate-57, 100 mg, 0.50 mmol), 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid (Intermediate-66, 161 mg, 0.60 mmol), oxalyl chloride (113 mg, 0.90 mmol), DMF (1 drop) and DIPEA (192 mg, 1.49 mmol) in CH2Cl2 (2 mL) to afford 10 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.32 (s, 1H), 8.71 (s, 1H), 8.64 (m, 1H), 8.48 (m, 2H), 8.08 (m, 3H), 7.53 (m, 1H), 7.23 (t, J=54 Hz, 1H), 4.44 (m, 1H), 4.41 (d, 2H), 2.50 (m, 1H), 1.27 (d, J=6.9 Hz, 6H), 1.04 (d, J=7.5 Hz, 6H); MS [M+H]+: 457.47.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-e024138fe08046e49637717465b01921
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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