Oxalyl chloride → 2-Chloro-5-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)benzamide

HRID 1469808노트

반응식

HRID 1469808 반응식
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:23][C:24]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:29][C:25]=1[C:26](O)=[O:27].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:29][C:25]=1[C:26]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)=[O:27]

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 71680392N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

생성물 1

HCID 716787172-Chloro-5-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinazolin-8-yl)benzamide수율 27.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (Intermediate-7, 50 mg, 0.164 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 88 mg, 0.326 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (63 mg, 0.49 mmol) in CH2Cl2 (2 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.24 (s, 1H), 10.16 (s, 1H), 8.83 (d, J=6.6 Hz, 1H), 8.69 (s, 1H), 8.33 (m, 2H), 8.23 (m, 2H), 7.75-7.55 (m, 4H), 7.50 (d, J=6.9 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 4.31 (d, J=5.4 Hz, 2H), 1.13 (s, 9H); MS [M+H]+: 556.23.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-521782071b2d495db3664833feb5cde5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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