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1,2-Dichloroethane → Tert-butyl 2-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]carbonyl}hydrazinecarboxylate

HRID 490884
ノート
印刷プレビュー

反応式

HRID 490884 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([OH:21])=O)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[NH:37][NH2:38]>CN(C=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([NH:38][NH:37][C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:21])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]
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 111,2-DichloroethaneHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 534878291-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

生成物 1

HCID 57675152Tert-butyl 2-{[1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]carbonyl}hydrazinecarboxylate収率 67.4%

試薬・触媒・溶媒

1
HCID 6228Dimethylformamide溶媒

実験手順

A suspension of Intermediate 17 (1.48 g), EDC (1.34 g) and HOBT (0.83 g) in DMF (20 ml) was stirred at room temperature for 30 min. t-Butyl carbazate (0.68 g) was then added and stirring continued under nitrogen for a further 66 h. The mixture was concentrated in vacuo and the residue divided into two portions for purification. Each portion was applied to an SPE cartridge (aminopropyl, 10 g) which was eluted with methanol and the combined eluents were concentrated in vacuo. Further purification was carried out by Biotage (silica, 40 g), eluting with cyclohexane:ethyl acetate (1:4). Fractions containing desired material were combined and concentrated in vacuo to afford Intermediate 18 (1.39 g). LCMS showed MH+=405; Tm=2.64 min.

後処理

  1. additionwas then added
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue divided into two portions for purification
  4. washwas eluted with methanol
  5. concentrationthe combined eluents were concentrated in vacuo
  6. customFurther purification
  7. washeluting with cyclohexane:ethyl acetate (1:4)
  8. additionFractions containing desired material
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5aeeff560ead445a94d25c3cb2aef2c5
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07528148B2

反応ノート

読み込み中…

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