Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzamide

HRID 1469855노트

반응식

HRID 1469855 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].[Cl:17][C:18]1[C:23]([C:24](O)=[O:25])=[C:22]([F:27])[C:21]([CH2:28][NH:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][OH:33])=[CH:20][CH:19]=1.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:24](=[O:25])[C:23]3[C:18]([Cl:17])=[CH:19][CH:20]=[C:21]([CH2:28][NH:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][OH:33])[C:22]=3[F:27])[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 866922636-Chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

생성물 1

HCID 71680056N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzamide수율 10.8%

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), 6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoic acid (Intermediate-59, 168 mg, 0.56 mmol), oxalyl chloride (116 mg, 0.92 mmol), DMF (1 drop) and DIPEA (178 mg, 1.37 mmol) in CH2Cl2 (2 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.41 (s, 1H), 8.68 (d, J=7.8 Hz, 1H), 8.51 (s, 1H), 8.17 (d, J=8.1 Hz, 1H), 8.11 (t, 1H), 7.52-7.38 (m, 4H), 4.91 (t, 1H), 4.33 (d, J=6.3 Hz, 2H), 3.42 (d, 2H), 1.55 (s, 9H), 1.08 (s, 6H); MS [M+H]+: 502.46.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-ea55583471834e1ca3ac205df8bc6e2f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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