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Hydrochloric Acid → HCID 178488248, 화합물

HRID 897848
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HRID 897848 반응식
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12.Cl.O1CCOCC1>C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 22347211N1-[4-(4-amino-1 trityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide

생성물 1

HCID 178488248HCID 178488248, 화합물수율 44.6%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
50 °C

실험 절차

A mixture of N1-[4-(4-amino-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (2.10 g, 1.75 mmol), 6 N aqueous hydrochloric acid (10 mL), p-dioxane (10 mL) and ethanol (8 mL) was heated at 50° C. for 6 hours. The mixture was filtered and the solid was washed with ethanol, dried in a vacuum oven over the weekend, and purified by flash column chromatography on silica to provide N1-[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.35 g, 0.78 mmol). The filtrate was concentrated and purified by flash column chromatography on silica and preparative HPLC to provide the same product N1-[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl]-2-fluoro-4-trifluoromethylbenzamide (0.67 g, 1.51 mmol) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 13.58 (s, 1H), 9.90 (dd, 1H), 8.30(d, 1H), 8.23 (s, 1H), 8.05 (t, 1H), 7.90 (d, 1H), 7.75 (d, 1H), 7.36 (s, 1H), 7.24 (d, 1H), 3.94 (s, 3H); MS: MH+ 447.

후처리

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with ethanol
  3. customdried in a vacuum oven over the weekend
  4. custompurified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-0a830cb37efa4ce591435f49ea65253e
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06921763B2

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