tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(5-carbamoyl-3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 730815Notes

Reaction equation

HRID 730815 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:3]2[C:2]([Cl:1])=[CH:10][C:6]([C:7](=[O:8])[NH2:9])=[CH:5][N:4]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27821675,6-Dichloropyridine-3-carboxamide

Product 1

HCID 11573673Tert-butyl 4-(5-carbamoyl-3-chloropyridin-2-yl)piperazine-1-carboxylate

Procedure

The nicotinamide from step (b) above (1.3 g, 6.8 mmol) and piperazine-1-carboxylic acid tert-butyl ester (1.27 g, 6.8 mmol, Aldrich) reacted under the conditions Example 3a to give the title compound as a light-yellow solid. MS (ESI, pos. ion) m/z: 341 (M+1).

Sources & evidence

ORD record
ord-0da4ea8a970c49aaaf0af1b4378dc3eb
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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