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

HRID 1056987ノート

反応式

HRID 1056987 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3b1c8ff346bf4480a685d1bcb9f0d23a
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

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