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

HRID 1911900Notes

Reaction equation

HRID 1911900 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-75bb374914d54006903a27d08a03ee1f
Source dataset
uspto-grants-2013_12
Patent number
US08604205B2

Reaction notes

Loading…