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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0

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1-Methylpiperazine → 9-Fluoro-2-(2-isopropyl-5-methyl-1,2,4-triazol-3-yl)-10-[1-(4-methylpiperazin-1-yl)ethyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 1530727

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HRID 1530727 반응식

Br[CH:2]([C:4]1[C:5]([F:27])=[CH:6][C:7]2[O:16][CH2:15][CH2:14][N:13]3[C:9](=[N:10][C:11]([C:17]4[N:18]([CH:23]([CH3:25])[CH3:24])[N:19]=[C:20]([CH3:22])[N:21]=4)=[CH:12]3)[C:8]=2[CH:26]=1)[CH3:3].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>O1CCOCC1>[F:27][C:5]1[C:4]([CH:2]([N:32]2[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]2)[CH3:3])=[CH:26][C:8]2[C:9]3[N:13]([CH:12]=[C:11]([C:17]4[N:18]([CH:23]([CH3:25])[CH3:24])[N:19]=[C:20]([CH3:22])[N:21]=4)[N:10]=3)[CH2:14][CH2:15][O:16][C:7]=2[CH:6]=1

참가 물질 실험 절차 후처리 출처 및 근거 반응 노트

참가 물질

5

반응물 3

HCID 531671-Methylpiperazine

HCID 81531Diisopropylethylamine

HCID 683131309-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

생성물 1

HCID 683131259-Fluoro-2-(2-isopropyl-5-methyl-1,2,4-triazol-3-yl)-10-[1-(4-methylpiperazin-1-yl)ethyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine수율 63.3%

시약·촉매·용매 1

HCID 31275

1,4-Dioxane

용매

실험 절차

A solution of 9-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 374 (99 mg, 0.23 mmol), N-methylpiperazine (28 μL, 0.25 mmol) and DIPEA (60 μL, 0.35 mmol) in dioxane (1 mL) was stirred at RT for 72 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (Si-PPC, gradient 0-8% 2 M NH3/MeOH in DCM) to give 66 mg of a pale yellow oil. The compound was further purified by reverse phase column chromatography (C18, gradient 2-50% MeOH in 1% TFA/H2O) and then loaded in MeOH onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 2 M NH3 in MeOH. The basic fraction was concentrated in vacuo to afford 373 (47 mg, 40% over 2 steps) as a white solid. LCMS (Method K): RT 2.70 min [M+H]+ 454.2. 1H NMR (CD3OD, 400 MHz): δ 8.54 (1H, d, J=8.6 Hz), 7.68 (1H, s), 6.76 (1H, d, J=11.0 Hz), 5.83 (1H, sept., J=6.7 Hz), 4.49 (4H, br s), 3.84 (1H, q, J=6.8 Hz), 2.47 (8H, br s), 2.33 (3H, s), 2.22 (3H, s), 1.53 (3H, d, J=6.7 Hz), 1.52 (3H, d, J=6.7 Hz), 1.40 (3H, d, J=6.8 Hz)

후처리

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by column chromatography (Si-PPC, gradient 0-8% 2 M NH3/MeOH in DCM)

출처 및 근거

ORD 기록: ord-24fadd5d87224038a85f25147b4d4acb
출처 데이터셋: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09090628B2

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