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

반응식

HRID 490905 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca21e630afde4d4291aae7deb4001f10
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528148B2

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