Thionyl Chloride → N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-(isobutyramidomethyl)benzamide

HRID 1469856노트

반응식

HRID 1469856 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:34])[CH:31]([CH3:33])[CH3:32])=[CH:20][CH:19]=1.S(Cl)(Cl)=O.CCN(C(C)C)C(C)C>C1COCC1>[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:34])[CH:31]([CH3:32])[CH3:33])[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 물질

6

반응물 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 866922656-Chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acidHCID 86692301N4-(tert-butyl)quinazoline-4,8-diamine

생성물 1

HCID 71680057N-(4-(tert-Butylamino)quinazolin-8-yl)-6-chloro-2-fluoro-3-(isobutyramidomethyl)benzamide수율 6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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), 6-chloro-2-fluoro-3-(isobutyramidomethyl)benzoic acid (Intermediate-60, 188 mg, 0.69 mmol), thionyl chloride (1 mL), and DIPEA (238 mg, 1.80 mmol) in THF (2 mL) to afford 13 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.69 (d, 1H), 8.50 (s, 1H), 8.37 (t, 1H), 8.15 (d, 1H), 7.52-7.40 (m, 4H), 4.32 (d, 2H), 1.55 (s, 9H), 1.03 (d, J=6.3 Hz, 6H); MS [M+H]+: 474.34.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-02146b0240aa4d0bb2b332de428e25dd
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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