Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-3-(pivalamidomethyl)benzamide

HRID 1469858노트

반응식

HRID 1469858 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:26]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:25]([F:35])[CH:24]=[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]=[CH:24][C:25]([F:35])=[C:26]([CH2:27][NH:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[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 866922712-Chloro-4-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

생성물 1

HCID 86692307N-(4-(tert-Butylamino)quinazolin-8-yl)-2-chloro-4-fluoro-3-(pivalamidomethyl)benzamide수율 5.4%

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-3-(pivalamidomethyl)benzoic acid (Intermediate-64, 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 12 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.05 (s, 1H), 8.71-8.69 (d, J=7.2 Hz, 1H), 8.49 (s, 1H), 8.15-8.13 (d, J=7.8 Hz, 1H), 7.83 (t, 1H), 7.75-7.73 (m, 1H), 7.53-7.47 (m, 2H), 7.40-7.34 (t, J=8.7 Hz, 1H), 4.43 (d, 2H), 1.54 (s, 9H), 1.08 (s, 9H); MS [M+H]+: 486.56.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-06e5ea2abba14952a97e44dfa86559e1
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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