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

HRID 2178973Notes

Reaction equation

HRID 2178973 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:16])[CH2:14][CH3:15].[C:17]([O:21][C:22](=[O:37])[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][N:31]=2)[CH2:25]1)([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22](=[O:37])[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=4)[N:5]=[CH:4][C:3]=3[C:13](=[O:16])[CH2:14][CH3:15])=[CH:32][N:31]=2)[CH2:25]1)([CH3:20])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 66715874(R)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamateHCID 897056421-(4,6-Dichloro-1,5-naphthyridin-3-yl)propan-1-one

Product 1

HCID 117798298(R)-tert-butyl (1-(5-((6-chloro-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamateYield 84.9%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)propan-1-one (500 mg, 1.96 mmol) was reacted with (R)-tert-butyl(1-(5-aminopyridin-2-yl)piperidin-3-yl)carbamate (860 mg, 2.94 mmol) to afford the desired product (850 mg, 84%) as a light brown solid: ESI MS m/z 511 [M+H]+.

Sources & evidence

ORD record
ord-a6627d3283d340b98ae5786748ddb867
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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