Dimethylformamide → tert-Butyl 1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-ylcarbamate

HRID 2233845Notes

Reaction equation

HRID 2233845 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]2)[CH:5]=[C:4]([C:22]([NH:24][NH2:25])=[O:23])[CH:3]=1.CN([CH:29]=[O:30])C>>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:13]2)[CH:5]=[C:4]([CH:22]2[N:24]=[N:25][C:29](=[O:30])[O:23]2)[CH:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 86608244tert-Butyl 1-[6-chloro-4-(hydrazinocarbonyl)pyridin-2-yl]piperidin-4-ylcarbamate2×

Product 1

HCID 86608245tert-Butyl 1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-ylcarbamate

Procedure

N,N′-Carbonyldiimidazole (0.12 g, 0.82 mmol) was added to a solution of tert-butyl 1-[6-chloro-4-(hydrazinocarbonyl)pyridin-2-yl]piperidin-4-ylcarbamate (Intermediate 49, 0.15 g, 0.41 mmol) in DMF (3 ml). The mixture was stirred at room temperature overnight and was purified by semi-preparative HPLC eluting with CH3CN/H2O (0.1% TFA) mixtures to afford the title compound (0.125 g).

Workup

  1. customwas purified by semi-preparative HPLC
  2. washeluting with CH3CN/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-46f94dbab38b4490a60e7999896fee63
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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