Water → 4-[4-(Cyclopropylmethoxy)-1-methyl-1H-indazol-5-yl]-6-methyl-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 1056987노트

반응식

HRID 1056987 반응식
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][O:12][C:13]2[C:21]([C:22]3[C:23]4[CH:32]=[N:31][N:30](COCC[Si](C)(C)C)[C:24]=4[C:25](=[O:29])[N:26]([CH3:28])[CH:27]=3)=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[N:16][N:17]3[CH3:41])[CH2:10][CH2:9]1.[OH-].[NH4+].O>C(Cl)Cl.CO>[CH:8]1([CH2:11][O:12][C:13]2[C:21]([C:22]3[C:23]4[CH:32]=[N:31][NH:30][C:24]=4[C:25](=[O:29])[N:26]([CH3:28])[CH:27]=3)=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[N:16][N:17]3[CH3:41])[CH2:10][CH2:9]1

참가 물질

7

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 1238389734-(4-(cyclopropylmethoxy)-1-methyl-1H-indazol-5-yl)-6-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-7(6H)-one

생성물 1

HCID 1180939404-[4-(Cyclopropylmethoxy)-1-methyl-1H-indazol-5-yl]-6-methyl-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one수율 67.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (0.564 mL) was added dropwise to a solution of 4-[4-(cyclopropylmethoxy)-1-methyl-1H-indazol-5-yl]-6-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.0549 g, 0.114 mmol) in methylene chloride (0.564 mL) and the resultant reaction mixture was stirred at RT for 30 min. The reaction mixture was concentrated in vacuo to yield a crude residue. The crude residue was dissolved in methanol (1.00 mL), followed by dropwise addition of 15.0 M solution of ammonium hydroxide in water (0.250 mL, 3.76 mmol). The resultant reaction mixture was stirred at RT for 30 min. The reaction mixture was purified via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (26.8 mg, 67%). 1H NMR (500 MHz, DMSO-d6) δ 14.00 (br s, 1H), 8.23 (s, 1H), 7.72 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.33 (d, J=8.5 Hz, 1H), 7.28 (s, 1H), 4.05 (d, J=6.8 Hz, 2H), 4.03 (s, 3H), 3.58 (s, 3H), 1.23-0.81 (m, 1H), 0.51-0.26 (m, 2H), 0.25-0.01 (m, 2H); LCMS calculated for C19H20N5O2 (M+H)+: m/z=350.2. found: 350.1.

후처리

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield a crude residue
  4. customThe resultant reaction mixture
  5. stirringwas stirred at RT for 30 min
  6. customThe reaction mixture was purified via preparative LCMS (XBridge C18 column
  7. washeluting with a gradient of acetonitrile/water 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

출처 및 근거

ORD 기록
ord-3b1c8ff346bf4480a685d1bcb9f0d23a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

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