Oxalyl chloride → 2-Chloro-N-(4-((4,4-difluorocyclohexyl)amino)quinazolin-8-yl)-5-(pivalamidomethyl)benzamide

HRID 1469809노트

반응식

HRID 1469809 반응식
[F:1][C:2]1([F:20])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH2:19])[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:27][C:23]=1[C:24](O)=[O:25].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])=[CH:27][C:23]=1[C:24]([NH:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[NH:8][CH:5]1[CH2:6][CH2:7][C:2]([F:1])([F:20])[CH2:3][CH2:4]1)=[O:25]

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 86692230N4-(4,4-difluorocyclohexyl)quinazoline-4,8-diamine

생성물 1

HCID 866922772-Chloro-N-(4-((4,4-difluorocyclohexyl)amino)quinazolin-8-yl)-5-(pivalamidomethyl)benzamide수율 21.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared following the procedure described in Example-1 using N4-(4,4-difluorocyclohexyl)quinazoline-4,8-diamine (Intermediate-9, 60 mg, 0.215 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 116 mg, 0.431 mmol), oxalyl chloride (81 mg, 0.65 mmol), DMF (1 drop) and DIPEA (84 mg, 0.65 mmol) in CH2Cl2 (3 mL) to afford 25 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.13 (s, 1H), 8.71 (d, 1H), 8.49 (s, 1H), 8.19 (m, 2H), 8.05 (d, 1H), 7.57-7.54 (m, 3H), 7.41 (d, 1H), 4.41 (m, 1H), 4.31 (d, 2H), 2.00 (m, 6H), 1.75 (m, 2H), 1.12 (s, 9H); MS (m/z): 530.20 (M+H)+.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-0d000e661d984affb9d5e963f35c1d2a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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