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

HRID 1469861노트

반응식

HRID 1469861 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-67a9824fdbb94d6d9a27913abd2d1066
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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