Triethyl orthoacetate → HCID 86608250, compound

HRID 2233850Notes

Reaction equation

HRID 2233850 reaction equation
[B].[NH2:2][C:3](=[N:25][OH:26])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]2)[CH:5]=1.[CH2:27](OC(OCC)(OCC)C)C>>[Cl:10][C:8]1[N:7]=[C:6]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:15][CH2:16]2)[CH:5]=[C:4]([C:3]2[N:2]=[CH:27][O:26][N:25]=2)[CH:9]=1

Participants

4

Reactant 3

HCID 66221Triethyl orthoacetateHCID 5462311BoronHCID 136335750HCID 136335750, compound2×

Product 1

HCID 86608250HCID 86608250, compound

Procedure

Boron trifluoroetherate (0.1 ml) was added to a solution of tert-butyl 1-{4-[amino (hydroxyimino)methyl]-6-chloropyridin-2-yl}piperidin-4-ylcarbamate (Intermediate 54) (0.254 g, 0.69 mmol) in 1,1,1-triethoxyethane (1.5 ml) at room temperature. The mixture was refluxed for 10 minutes. The mixture was purified by flash chromatography on silica gel eluting with (n-hexanes:EtOAc; 70:30) to afford the title compound (50 mg).

Workup

  1. temperatureThe mixture was refluxed for 10 minutes
  2. customThe mixture was purified by flash chromatography on silica gel eluting with (n-hexanes:EtOAc; 70:30)

Sources & evidence

ORD record
ord-71188676839640c8b867bb5377dbe73f
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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