2-(Methylamino)ethanol → Benzyl (S)-2-[6-hydroxy-7-[(2-hydroxyethyl)methylamino]-1H-indazol-1-yl]-1-methylethylcarbamate

HRID 915746

反応式

Br[C:2]1[C:3]([OH:25])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13])[N:8]=[CH:7]2.[CH3:26][NH:27][CH2:28][CH2:29][OH:30]>[Cl-].[NH4+]>[OH:25][C:3]1[C:2]([N:27]([CH2:28][CH2:29][OH:30])[CH3:26])=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:5][CH:4]=1

参加物

反応条件

温度: 80 °C

実験手順

To a stirred solution of the product from Step A (0.24 g, 0.59 mmol) was added 2-(methyamino)ethanol (2.0 mL) and the solution was heated at 80° C. for 18 h. A saturated aqueous solution of ammonium chloride (20 mL) was added to the reaction mixture, which was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated to give a residue which was purified by chromatography (silica, 30% ethyl acetate in hexane) to give an oil (0.16 g, 68%): 1H NMR (CDCl3) δ 8.50 (1H, brs), 8.01 (1H, s), 7.30 (6H, m), 6.77 (1H, d, J=8.4 Hz), 5.02 (2H, m), 4.59 (2H, m), 4.77 (1H, brs), 4.09 (1H, m), 3.69 (1H, m), 3.36 (2H, m), 2.93 (3H, s), 1.26 (3H, d, J=6.4 Hz); MS (ES) m/z 399 (M+).

後処理

extractionwas extracted with ethyl acetate (3×50 mL)
washThe combined extracts were washed with brine (10 mL)
dry with materialdried (MgSO4)
customevaporated
customto give a residue which
customwas purified by chromatography (silica, 30% ethyl acetate in hexane)

出典と根拠

ORDレコード: ord-bf0826c99f774a3c819f5b0963c970a3
出典データセット: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07268131B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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