1,2-Dichloroethane → 2,2-Dimethylpropanoyl-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490905

反応式

HRID 490905 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH3:22])=[C:10]([C:19](O)=[O:20])[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:34]=[N:33]C=2C=1.[C:37](NN)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>CN(C=O)C>[CH3:39][C:38]([CH3:41])([CH3:40])[C:37]([C:5]1[C:6]2[C:7](=[N:8][C:9]([CH3:22])=[C:10]([C:19]([NH:33][NH2:34])=[O:20])[C:11]=2[NH:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:3]([CH2:1][CH3:2])[N:4]=1)=[O:42]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5451472,2-DimethylpropanehydrazideHCID 576751871-Ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

生成物 1

HCID 866089802,2-Dimethylpropanoyl-ethyl-6-methyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide収率 79.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Intermediate 60 (0.255 g, 0.84 mmol), EDC (0.225 g, 1.17 mmol) and HOBT (0.136 g, 1.0 mmol) in DMF (5 ml) was stirred at 20° C. for 75 minutes. Pivalic acid hydrazide (0.107 g, 0.92 mmol) was added and stirring continued for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM and water. The organic phase was washed with aqueous sodium hydrogen carbonate then evaporated in vacuo to afford Intermediate 61 as a white solid (0.27 g).). LCMS showed MH+=403; TRET=2.13 min.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and water
  3. washThe organic phase was washed with aqueous sodium hydrogen carbonate
  4. customthen evaporated in vacuo

出典と根拠

ORDレコード
ord-ca21e630afde4d4291aae7deb4001f10
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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