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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide

HRID 1969808
ノート
印刷プレビュー

反応式

HRID 1969808 の反応式
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1)[NH2:2].[CH2:22]([CH:24]1[CH2:28][CH:27]([O:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH2:26][CH:25]1[C:36](O)=[O:37])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:22]([CH:24]1[CH2:28][CH:27]([O:29][CH:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[CH2:26][CH:25]1[C:36]([NH:2][NH:1][C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:13])=[O:14])[C:6]2=[N:7][CH:8]=1)=[O:37])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazineHCID 585577642-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentanecarboxylic acid

生成物 1

HCID 585579512-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)-N'-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide収率 74.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.233 g, 0.767 mmol, WO2009152133 Preparation #9) and 2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)cyclopentanecarboxylic acid (0.190 g, 0.767 mmol) in DCM (8.00 mL) was added HATU (0.350 g, 0.920 mmol, Novabiochem) and TEA (0.43 mL, 3.07 mmol). The resulting suspension was stirred at ambient temperature for about 4 h. The reaction was partitioned between DCM (50 mL) and water (25 mL) and the layers were separated. The organic layer was washed with water (2×25 mL) and brine (30 mL), dried over anhydrous MgSO4, filtered, and concd to give a brown residue. The crude material was purified by silica gel chromatography using a gradient of 1-10% MeOH in DCM to give 2-ethyl-4-(tetrahydro-2H-pyran-4-yloxy)-N′-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)cyclopentanecarbohydrazide (0.300 g, 74%); LC/MS (Table 1, Method b) Rt=2.20 min; MS m/z: 528 (M+H)+.

後処理

  1. customThe reaction was partitioned between DCM (50 mL) and water (25 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with water (2×25 mL) and brine (30 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customconcd to give a brown residue
  7. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-dc8434b47878488db922f12156050c9c
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426411B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート