Methylhydrazine → 4-(Cyclopentylamino)-1-ethyl-N-[methyl]-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

HRID 490876노트

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HRID 490876 반응식
[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.CN(C(O[N:29]1[N:37]=NC2C=CC=C[C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CNN>CN(C=O)C.C(Cl)CCl>[CH:1]1([NH:6][C:7]2[C:12]([C:13]([N:29]([CH3:30])[NH2:37])=[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

참가 물질

8

반응물 5

HCID 6061MethylhydrazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576751554-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid2회

생성물 1

HCID 576751694-(Cyclopentylamino)-1-ethyl-N-[methyl]-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매2회

실험 절차

Intermediate 3 (0.10 g) was dissolved in DMF (2 ml) and treated with HBTU (0.136 g) and DIPEA (0.116 g). A separate portion of Intermediate 3 (0.10 g) was dissolved in DMF (2 ml) and treated with EDC (0.096 g) and HOBT (0.058 g). The resultant suspensions were both stirred under nitrogen for 15 min, then methyl hydrazine (0.017 g) added to each and stirring continued under nitrogen for 18 h. The mixtures were independently concentrated in vacuo and the residues partitioned between DCM and water. The organic layers were concentrated and each applied to an SPE cartridge (aminopropyl, 2 g) which was eluted with methanol, followed by 10% ammonia in methanol. The two portions of Intermediate 7 thus afforded were combined (0.16 g). LCMS showed MH+=303; TRET=2.22 min.

후처리

  1. stirringstirring
  2. waitcontinued under nitrogen for 18 h
  3. concentrationThe mixtures were independently concentrated in vacuo
  4. customthe residues partitioned between DCM and water
  5. concentrationThe organic layers were concentrated
  6. washwas eluted with methanol

출처 및 근거

ORD 기록
ord-a396932381784cdaa7c001dcef5ed58b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528148B2

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