3-Piperidinone, 1-(phenylmethyl)- → N5-(1-Benzylpiperidin-3-yl)-1H-indazole-3,5-diamine

HRID 1912008Notes

Reaction equation

HRID 1912008 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][C:28](=O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+]>CO>[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([NH:11][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[NH2:1])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 5003444Sodium cyanoborohydrideHCID 23571038tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

Product 1

HCID 57446051N5-(1-Benzylpiperidin-3-yl)-1H-indazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of tert-butyl 3,5-diamino-1H-indazole-1-carboxylate with 1-benzylpiperidin-3-one using the method of Example 8, with the modification that sodium cyanoborohydride was used as the reductant and methanol was used as the solvent, followed by deprotection using the method of Example 4 afforded the title compound.

Sources & evidence

ORD record
ord-8e7a02be265447238b8ee4bac7d6890d
Source dataset
uspto-grants-2013_12
Patent number
US08604218B2

Reaction notes

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