4-Methoxybenzylamine → tert-Butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

HRID 505498ノート

反応式

HRID 505498 の反応式
F[C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:9]=[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>CN1C(=O)CCC1.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:8]2[C:6]3=[N:7][C:2]([NH:34][CH2:33][C:32]4[CH:35]=[CH:36][C:29]([O:28][CH3:27])=[CH:30][CH:31]=4)=[CH:3][CH:4]=[C:5]3[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:9]2)=[CH:20][CH:21]=1

参加物

5

反応物 2

HCID 754524-MethoxybenzylamineHCID 56833644tert-Butyl 6-fluoro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

生成物 1

HCID 56834061tert-Butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To a solution of tert-butyl 6-fluoro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (2.55 g, 7.14 mmol) in NMP (30 mL) was added 4-methoxybenzylamine (2.80 mL, 21.41 mmol). The resulting mixture was then heated to 80° C. for 2 hours, after which the mixture was diluted with water (200 mL) and extracted with EtOAc (2×200 mL). The combined extracts were washed with water (100 mL), dried with MgSO4, filtered, absorbed onto silica gel (17 g) and removed the solvent in vacuo. This solid was purified on silica gel (80 g) column (0-100% EtOAc/CH2Cl2 to give the title compound. LRMS (M+1)=474.0

後処理

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe combined extracts were washed with water (100 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customabsorbed onto silica gel (17 g)
  6. customremoved the solvent in vacuo
  7. customThis solid was purified on silica gel (80 g) column (0-100% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-5020448ab9594d92a887b8624969bbe8
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

読み込み中…