1-Piperazinecarboxylic acid, ethyl ester → HCID 11703655, compound

HRID 639801Notes

Reaction equation

HRID 639801 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([N:8]2[N:12]=[N:11][C:10]([CH:13](OS(C)(=O)=O)[CH3:14])=[N:9]2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])[CH3:28]>C(#N)C>[CH2:27]([O:29][C:30]([N:32]1[CH2:33][CH2:34][N:35]([CH:13]([C:10]2[N:11]=[N:12][N:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[F:20])[N:9]=2)[CH3:14])[CH2:36][CH2:37]1)=[O:31])[CH3:28]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 86602448HCID 86602448, compound

Product 1

HCID 11703655HCID 11703655, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (25.2 mg, 72%, yellow oil, ˜90% pure) was prepared from methanesulfonic acid 1-[2-(5-chloro-2-fluoro-phenyl)-2H-tetrazol-5-yl]-ethyl ester (˜29.5 mg, 0.09 mmol) using potassium carbonate (38 mg, 0.27 mmol) and 1-ethoxycarbonyl piperazine (20 uL, 0.14 mmol) in acetonitrile (1.5 mL) at 80° C. overnight. The product was purified by chromatography using a silica SPE tube (25-35% ethyl acetate in hexane). 1H NMR (CDCl3) δ (ppm): 7.91 (dd, 1H), 7.51 (ddd, 1H), 7.33 (t, 1H), 4.32 (q, 1H), 4.11 (q, 2H), 3.52 (m, 4H), 2.61 (m, 2H), 2.51 (m, 2H), 1.65 (d, 3H), 1.24 (t, 3H).

Workup

  1. customat 80° C.
  2. customovernight
  3. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-126f7565b47a4dafb31434cdcfea97a7
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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