Oxalyl chloride → 6-Chloro-2-fluoro-N-(7-methyl-4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)-3-(pivalamidomethyl)benzamide

HRID 1469831노트

반응식

HRID 1469831 반응식
[CH3:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([C:6]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:24][C:25]1[C:30]([C:31](O)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:27][CH:26]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:24][C:25]1[C:30]([C:31]([NH:12][C:11]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]3[C:10]=2[N:9]=[CH:8][N:7]=[C:6]3[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 673386327-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

생성물 1

HCID 716793926-Chloro-2-fluoro-N-(7-methyl-4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)-3-(pivalamidomethyl)benzamide수율 9.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-37, 140 mg, 0.44 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 163 mg, 0.57 mmol), oxalyl chloride (108 mg, 0.86 mmol), DMF (1 drop) and DIPEA (170 mg, 1.32 mmol) in CH2Cl2 (5 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.71 (s, 1H), 10.03 (s, 1H), 8.72 (s, 1H), 8.46 (d, J=8.4 Hz, 1H), 8.35 (s, 1H), 8.27 (d, J=9.3 Hz, 1H), 8.19 (t, 1H), 7.66-7.63 (m, 2H), 7.46 (d, J=6.9 Hz, 1H), 7.40 (d, J=8.7 Hz, 1H), 7.31 (t, J=8.1 Hz, 1H), 4.33 (d, J=5.4 Hz, 2H), 2.50 (s, 3H), 1.15 (s, 9H); MS (m/z): 588.23 (M)+.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-567e223c8dc64a7ab38b33c6e5405328
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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