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Water → HCID 58299982, 화합물

HRID 875960
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HRID 875960 반응식
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.C(O[C:36]1(O[Si](C)(C)C)[CH2:38][CH2:37]1)C.C([BH3-])#N.[Na+]>C1COCC1.C(O)(=O)C>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([CH:36]6[CH2:38][CH2:37]6)[CH2:24][CH2:23]5)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1
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참가 물질

7

반응물 4

HCID 962WaterHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 441325859-Cyclopentyl-N-(5-Piperazin-1-Ylpyridin-2-Yl)pyrido[4,5]pyrrolo[1,2-D]pyrimidin-2-Amine

생성물 1

HCID 58299982HCID 58299982, 화합물수율 26.4%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of compound 7 (207 mg, 0.50 mmol) in THF (5 mL) were added water (0.05 mL), (1-ethoxy-1-cyclopropyloxy)-trimethylsilane (1174 mg, 1.0 mmol), acetic acid (0.55 mL) and sodium cyanoborohydride (1 mL, 1 M in THF, 1.0 mmol). The mixture was stirred at 60° C. overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and washed with saturated NaHCO3 and brine then dried. The solvent was evaporated and the residue was purified by chromatography on silica gel eluting with CH2Cl2:methanol:NH4OH (400:10:1) to give compound 187 as a yellow solid (60 mg, 26% yield). 1H NMR (500 MHz, CDCl3) δ 9.08 (1H, s), 8.90 (1H, s), 8.51 (1 H, d, J=5 Hz), 8.39 (1H, d, J=10 Hz), 8.18 (1H, bs), 8.07 (1H, d, J=2 Hz), 7.84 (1H, d, J=5 Hz), 7.39 (1H, dd, J=10 Hz, J=2 Hz), 5.38 (1H, p, J=10 Hz), 3.17 (4H, q, J=5 Hz), 2.83 (2H, t, J=5 Hz), 2.42 (2H, m), 2.21-2.14 (4H, m), 1.88 (2H, m), 1.71 (1H, m), 0.53-0.46 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 454.2, Calculated 454.3.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3 and brine
  4. customthen dried
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography on silica gel eluting with CH2Cl2:methanol:NH4OH (400:10:1)

출처 및 근거

ORD 기록
ord-00f1824f46ba4a739e09c527fed7bf05
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980903B2

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