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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol

HRID 1969623
ノート
印刷プレビュー

反応式

HRID 1969623 の反応式
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([CH:20]=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl[C:57]1[C:58](=[O:69])[C:59](C#N)=[C:60]([C:65]#N)[C:61](=O)[C:62]=1Cl>C(Cl)Cl.O>[CH2:61]([CH:60]1[CH:65]([C:20]2[N:19]3[C:14]4[CH:13]=[CH:12][N:11]([S:1]([C:4]5[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=5)(=[O:2])=[O:3])[C:15]=4[N:16]=[CH:17][C:18]3=[N:22][N:21]=2)[CH2:57][CH:58]([OH:69])[CH2:59]1)[CH3:62]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 585574426-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

生成物 1

HCID 585575563-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol
収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To 2-ethyl-4-(4-methoxybenzyloxy)cyclopentyl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (1.153 g, 2.11 mmol, prepared using Z from Preparation #EE.1, A from Example #1, Step D, HATU, and TEA, B with DIEA) in DCM (18 mL) and water (3.5 mL) was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (0.576 g, 2.54 mmol). The reaction mixture was stirred at ambient temperature for about 16 h. The solid was removed by filtration while washing with DCM (150 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 (2×40 mL) and brine (40 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified using silica gel chromatography (40 g) eluting with a gradient of 30-100% EtOAc in DCM to give 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (0.672 g, 75%): LC/MS (Table 1, Method b) Rt=2.09 min; MS m/z: 426 (M+H)+.

後処理

  1. customfrom Preparation #EE.1
  2. customThe solid was removed by filtration
  3. washwhile washing with DCM (150 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3 (2×40 mL) and brine (40 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe residue was purified
  9. washeluting with a gradient of 30-100% EtOAc in DCM

出典と根拠

ORDレコード
ord-09dffd1d1a6048ddb97e3641709f70ea
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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