1,2-Dichloroethane → 4-(Cyclopentylamino)-1-ethyl-N'-isobutyryl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490877

反応式

HRID 490877 の反応式
[CH:1]1([NH:6][C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:35]([NH:40][NH2:41])(=[O:39])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C>[CH:1]1([NH:6][C:7]2[C:12]([C:13]([NH:41][NH:40][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])=[O:15])=[CH:11][N:10]=[C:9]3[N:16]([CH2:19][CH3:20])[N:17]=[CH:18][C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 192392-MethylpropanehydrazideHCID 757711-HydroxybenzotriazoleHCID 576751554-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

生成物 1

HCID 576751924-(Cyclopentylamino)-1-ethyl-N'-isobutyryl-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Intermediate 3 (0.060 g), EDC (0.06 g) and HOBT (0.035 g) were suspended in DMF (2 ml) and stirred under nitrogen for 15 minutes. Isobutyric acid hydrazide (0.027 g) was then added and the mixture stirred under nitrogen for 18 h. Solvents were removed in vacuo and the residue partitioned between DCM and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution, then concentrated in vacuo and applied to an SPE cartridge (aminopropyl, 1 g) which was eluted with methanol. Concentration in vacuo afforded Intermediate 10. LCMS showed MH+=359; TRET=2.70 min.

後処理

  1. stirringthe mixture stirred under nitrogen for 18 h
  2. customSolvents were removed in vacuo
  3. customthe residue partitioned between DCM and water
  4. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution
  5. concentrationconcentrated in vacuo
  6. washwas eluted with methanol
  7. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-4a9655ea6f8640b3bb2a4d9c0eecd8dc
出典データセット
uspto-grants-2009_05
特許番号
US07528148B2

関連ノート

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