tert-Butyl piperazine-1-carboxylate → 6-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-5-chloropyridine-3-carboxylic acid

HRID 912871Notes

Reaction equation

HRID 912871 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH: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]([OH:9])=[O:8])=[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 2479875,6-Dichloronicotinic acid

Product 1

HCID 116098286-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-5-chloropyridine-3-carboxylic acid

Procedure

5,6-Dichloro-nicotinic acid (5.0 g, 0.026 mol, Aldrich) reacted with piperazine-1-carboxylic acid tert-butyl ester (4.87 g, 0.026 mol, Aldrich) under the conditions of Example 3a to give the title compound as yellow semi-solid, which was used in the next step without further purification. MS (ESI, neg. ion) m/z: 340 (M−1).

Sources & evidence

ORD record
ord-0a2fcfdb9f2f4b7ab8a740d5877992be
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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