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

HRID 490876Notes

Reaction equation

HRID 490876 reaction equation
[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

Participants

8

Reactant 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 acid2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a396932381784cdaa7c001dcef5ed58b
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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