Hydrochloric Acid → [1-((r)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-(4-methylsulfanyl-phenyl)-amine

HRID 1726309Notes

Reaction equation

HRID 1726309 reaction equation
[C:1]([CH2:3][C@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=2)[C:13](=O)[C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[N:16][CH:15]=2)[CH2:8][CH2:7]1)[CH3:5])#[N:2].B.C1COCC1.Cl>C1COCC1>[NH2:2][CH2:1][CH2:3][C@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[CH3:20])[C:22]2[CH:23]=[CH:24][C:25]([S:28][CH3:29])=[CH:26][CH:27]=2)[CH2:8][CH2:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68973020N-[1-((R)-2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-(4-methylsulfanyl-phenyl)-nicotinamide

Product 1

HCID 68970793[1-((r)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-(4-methylsulfanyl-phenyl)-amineYield 72.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above amide (276 mg, 0.70 mmol) in THF (10 mL) was reduced with BH3-THF (1.0M in THF, 4.2 mL, 4.2 mmol) at reflux and treated with 6N HCl (8 mL) to afford [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-(4-methylsulfanyl-phenyl)-amine as a clear oil (203 mg, 70%) after basic work-up and purification.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-fc7eff61e55244fcbb145b4157f3b5a9
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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