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

HRID 1469862노트

반응식

HRID 1469862 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-e024138fe08046e49637717465b01921
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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