Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-5-(pivalamidomethyl)benzamide

HRID 1469857노트

반응식

HRID 1469857 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[CH:26]=[C:25]([F:27])[C:24]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[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>[C:1]([NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:20](=[O:21])[C:19]3[CH:23]=[C:24]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:33])([CH3:34])[CH3:32])[C:25]([F:27])=[CH:26][C:18]=3[Cl: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 866922682-Chloro-4-fluoro-5-(pivalamidomethyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

생성물 1

HCID 86692306N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-5-(pivalamidomethyl)benzamide수율 8.9%

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-chloro-4-fluoro-5-(pivalamidomethyl)benzoic acid (Intermediate-63, 159 mg, 0.56 mmol), oxalyl chloride (117 mg, 0.93 mmol), DMF (1 drop) and DIPEA (178 mg, 1.38 mmol) in CH2Cl2 (5 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.18 (s, 1H), 8.69-8.66 (d, J=7.2 Hz, 1H), 8.47 (s, 1H), 8.16-8.11 (m, 2H), 7.62-7.57 (m, 2H), 7.52-7.45 (m, 2H), 4.31-4.29 (d, J=5.7 Hz, 2H), 1.53 (s, 9H), 1.10 (s, 9H); MS [M+H]+: 486.45.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-9f1fa6e53a844da88c0a9f3ad471bbc3
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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