2-Acetamido-5-aminopyridine → N-{5-[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-ylamino]-pyridin-2-yl}-acetamide

HRID 1726240Notes

Reaction equation

HRID 1726240 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.O=[C:13]1[CH2:18][CH2:17][N:16]([C@H:19]([CH3:23])[CH2:20][C:21]#[N:22])[CH2:15][CH2:14]1>>[NH2:22][CH2:21][CH2:20][C@H:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=2)[CH2:14][CH2:15]1)[CH3:23]

Participants

3

Reactant 2

HCID 27352192-Acetamido-5-aminopyridineHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 68972845N-{5-[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-ylamino]-pyridin-2-yl}-acetamide

Procedure

Using general procedure A with N-(5-amino-pyridin-2-yl)-acetamide (Bae, Jong Woo; et al., Tetrahedron Lett., 41, 2, 2000, 175-178) (1.00 g, 6.62 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (1.16 g, 6.95 mmol) and then using general procedure J afforded N-{5-[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-ylamino]-pyridin-2-yl}-acetamide as a white solid (1.05 g, 52% over 2 steps).

Sources & evidence

ORD record
ord-1fa7d874274a4702a779b0b1a4229159
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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