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Oxalyl chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzamide

HRID 1469865
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HRID 1469865 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:23]([C:24](O)=[O:25])=[C:22]([F:27])[C:21]([CH2:28][NH:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][F:33])=[CH:20][CH:19]=1.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:24](=[O:25])[C:23]3[C:18]([Cl:17])=[CH:19][CH:20]=[C:21]([CH2:28][NH:29][C:30](=[O:36])[C:31]([CH3:35])([CH3:34])[CH2:32][F:33])[C:22]=3[F:27])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 866922736-Chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

생성물 1

HCID 71680230N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzamide수율 25.9%

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, 50 mg, 0.23 mmol), 6-chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzoic acid (Intermediate-67, 84 mg, 0.27 mmol), oxalyl chloride (52 mg, 0.41 mmol), DMF (1 drop) and DIPEA (89 mg, 0.69 mmol) in CH2Cl2 (2 mL) to afford 30 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.41 (s, 1H), 8.69-8.66 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.33 (t, 1H), 8.18-8.15 (d, J=9.3 Hz, 1H), 7.54-7.34 (m, 4H), 4.48-4.33 (m, 4H), 1.55 (s, 9H), 1.16 (s, 6H); MS (m/z): 504.64 (M+H)+.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-e5860bee58844dcd864978578c819ecf
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006257B2

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