(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 2178976Notes

Reaction equation

HRID 2178976 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].[C:18]([O:22][C:23](=[O:38])[NH:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][N:32]=2)[CH2:26]1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23](=[O:38])[NH:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][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:17])[CH:14]([CH3:16])[CH3:15])=[CH:33][N:32]=2)[CH2:26]1)([CH3:21])([CH3:19])[CH3:20]

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-6c393151f1e047839301affb22e96135
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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