(R)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate → (R)-tert-butyl (1-(5-((6-chloro-3-isobutyryl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate

HRID 526256Notes

Reaction equation

HRID 526256 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15].[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]2)=[N:23][CH:24]=1>>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:2]2[NH:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:26]2)=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 66715874(R)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamateHCID 1177728531-(4,6-Dichloro-1,5-naphthyridin-3-yl)-2-methylpropan-1-one

Product 1

HCID 117798299(R)-tert-butyl (1-(5-((6-chloro-3-isobutyryl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamateYield 90.6%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)-2-methylpropan-1-one (500 mg, 1.85 mmol) was reacted with (R)-tert-butyl (1-(5-aminopyridin-2-yl)piperidin-3-yl)carbamate (815 mg, 2.78 mmol) to afford the desired product (880 mg, 88%) as a red solid: ESI MS m/z 525 [M+H]+.

Sources & evidence

ORD record
ord-16ad35bafcd8438199f76d13a1fd9ab6
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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