Hydrochloric Acid → N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride

HRID 246665ノート

反応式

HRID 246665 の反応式
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24](COCC[Si](C)(C)C)[N:23]=[CH:22]4)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:34]>O1CCOCC1>[ClH:34].[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][N:23]=[CH:22]4)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 71280304N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

生成物 1

HCID 71280039N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride収率 21%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of N-tert-butyl-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (120 mg, 0.258 mmol) in dioxane (20 mL) was bubbled HCl gas until saturation and the reaction stirred at room temperature for 16 hours. Reaction mixture was concentrated and the residue purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions are: 40% acetonitrile/60% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min.). Concentrated HCl was added to the combined fractions containing pure product, then solvents evaporated to afford N-tert-butyl-2-(1H-indazol-7-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (20 mg, 21%) as a yellow solid. LCMS: (M+H)+=335; 1H NMR (300 MHz, CD3OD): δ 8.94 (s, 1H), 8.34 (s, 1H), 8.31 (s, 1H), 7.97 (s, 1H), 7.94 (s, 1H), 7.39 (t, 1H, J=6.9 Hz), 1.52 (s, 9H).

後処理

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customthe residue purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  4. wait40% acetonitrile/60% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min.
  5. additionConcentrated HCl was added to the combined fractions
  6. additioncontaining pure product
  7. customsolvents evaporated

出典と根拠

ORDレコード
ord-bf1c92712c134bae85e7087fec186bf8
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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