(R)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate → (R)-tert butyl [1-(5-{[6-chloro-3-(cyclopropanecarbonyl)-1,5-naphthyridin-4-yl]amino}pyridin-2-yl)piperidin-3-yl]carbamate

HRID 2178957Notes

Reaction equation

HRID 2178957 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]([CH:15]1[CH2:17][CH2:16]1)=[O:14].[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]([CH:15]3[CH2:17][CH2:16]3)=[O:14])=[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 897056244,6-Dichloro-1,5-naphthyridin-3-yl(cyclopropyl) methanone

Product 1

HCID 117798300(R)-tert butyl [1-(5-{[6-chloro-3-(cyclopropanecarbonyl)-1,5-naphthyridin-4-yl]amino}pyridin-2-yl)piperidin-3-yl]carbamateYield 76.5%

Procedure

Following general procedure I, 4,6-dichloro-1,5-naphthyridin-3-yl(cyclopropyl) methanone (400 mg, 1.5 mmol) was reacted with (R)-tert-butyl[1-(5-aminopyridin-2-yl) piperidine-3-yl]carbamate (550 mg, 1.9 mmol) to afford the product (600 mg, 76%) as an orange foam: ESI MS m/z 523 [M+H]+.

Sources & evidence

ORD record
ord-736f8103e2e24c879f276a9560e272a6
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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