Water → 4-(morpholin-4-yl)-5-[3-(1,2,4-oxadiazol-3-yl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 1750302노트

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HRID 1750302 반응식
[CH:1](OCC)(OCC)OCC.B(F)(F)F.CCOCC.[OH:20][N:21]=[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:38]3[C:37]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[N:36][CH:35]=[N:34][C:33]=3[N:32](COCC[Si](C)(C)C)[CH:31]=2)[CH:25]=1)[NH2:23].O>O1CCCC1>[N:39]1([C:37]2[C:38]3[C:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:22]5[N:23]=[CH:1][O:20][N:21]=5)[CH:25]=4)=[CH:31][NH:32][C:33]=3[N:34]=[CH:35][N:36]=2)[CH2:40][CH2:41][O:42][CH2:43][CH2:44]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 86706972HCID 86706972, 화합물

생성물 1

HCID 867069734-(morpholin-4-yl)-5-[3-(1,2,4-oxadiazol-3-yl)phenyl]-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

Triethyl orthoformate (760 mg, 5.1 mol) and boron trifluoride diethyl etherate (370 mg, 2.6 mol) were added to a 0° C. solution of N′-hydroxy-3-[4-(morpholin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzenecarboximidamide (C35) (600 mg, 1.3 mmol) in tetrahydrofuran (25 mL). The reaction mixture was heated at 40° C. for 18 hours, then poured into water (50 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated. Purification via preparative reversed phase high-performance liquid chromatography (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: aqueous ammonia, pH 10; Mobile phase B: acetonitrile; Gradient: 30% to 50% B) provided the product as a yellow solid. Yield: 62 mg, 0.18 mmol, 14%. LCMS m/z 349.0 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 9.77 (s, 1H), 8.40 (s, 1H), 8.24 (br s, 1H), 7.98 (br d, J=7.5 Hz, 1H), 7.82 (br d, J=7.3 Hz, 1H), 7.63-7.70 (m, 2H), 3.39-3.45 (m, 4H), 3.13-3.20 (m, 4H).

후처리

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via preparative reversed phase high-performance liquid chromatography (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: aqueous ammonia, pH 10; Mobile phase B: acetonitrile; Gradient: 30% to 50% B)

출처 및 근거

ORD 기록
ord-39a8e98ef65f4abab14702b2ab48e2fa
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156845B2

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