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Sodium hydride → tert-butyl 3-{1-[4-(methoxycarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-5-[(6-oxo-3-pyridin-4-ylpyridazin-1(6H)-yl)methyl]-1H-indazole-1-carboxylate

HRID 1520067
ノート
印刷プレビュー

反応式

HRID 1520067 の反応式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1.Br[CH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:22]=[C:21]2[C:34]1[N:35]=[N:36][N:37]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([O:47][CH3:48])=[O:46])=[CH:41][CH:40]=2)[CH:38]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:48][O:47][C:45]([C:42]1[CH:43]=[CH:44][C:39]([N:37]2[CH:38]=[C:34]([C:21]3[C:20]4[C:24](=[CH:25][CH:26]=[C:18]([CH2:17][N:13]5[C:12](=[O:15])[CH:11]=[CH:10][C:9]([C:6]6[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=6)=[N:14]5)[CH:19]=4)[N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[N:22]=3)[N:35]=[N:36]2)=[CH:40][CH:41]=1)=[O:46]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27276126-(Pyridin-4-yl)pyridazin-3(2H)-oneHCID 67981095tert-butyl 5-(bromomethyl)-3-{1-[4-(methoxycarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole-1-carboxylate

生成物 1

HCID 68061164tert-butyl 3-{1-[4-(methoxycarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-5-[(6-oxo-3-pyridin-4-ylpyridazin-1(6H)-yl)methyl]-1H-indazole-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Sodium hydride (106 mg; 2.43 mmol; 7.4 eq.) was added in one portion to a solution of 6-pyridin-4-ylpyridazin-3(2H)-one (176 mg; 1.02 mmol; 3.1 eq.) in DMF (6 mL). After 10 min a solution of tert-butyl 5-(bromomethyl)-3-{1-[4-(methoxycarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole-1-carboxylate (565 mg; 0.33 mmol; 1.0 eq.) in DMF (6 mL) was added dropwise over 2 min and the reaction solution stirred for 4 h at RT. The reaction mixture was then poured into saturated solution of NaHCO3 and extracted with EtOAc. Combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude was purified by preparative HPLC to give the title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 9.69 (s, 1H), 8.75-8.62 (m, 3H), 8.30 (d, J=8.8 Hz, 2H), 8.24-8.18 (m, 3H), 8.15 (d, J=9.2 Hz, 1H), 7.93 (dd, J=1.6, 4.6 Hz, 2H), 7.78-7.72 (m, 1H), 7.19 (d, J=9.8 Hz, 1H), 5.59 (s, 2H), 3.92 (s, 3H), 1.68 (s, 9H). MS (ESI+): 605.3.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialCombined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by preparative HPLC

出典と根拠

ORDレコード
ord-e355d4ed29d940f0b124e582108779d7
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073892B2

反応ノート

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