Triethylamine → 2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1791361Notes

Reaction equation

HRID 1791361 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N(CC)CC)C.[C:33]([C:35]1[CH:36]=[C:37]([CH:42]=[CH:43][CH:44]=1)[C:38]([NH:40]O)=[NH:39])#[N:34]>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:9]1[C:15]1[O:17][N:40]=[C:38]([C:37]2[CH:42]=[CH:43][CH:44]=[C:35]([C:33]#[N:34])[CH:36]=2)[N:39]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 14482387rac-(2R,6R)-1-[(tert-butoxy)carbonyl]-6-methylpiperidine-2-carboxylic acidHCID 178509779HCID 178509779, compound

Product 1

HCID 100219472-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-piperidine-1-carboxylic acid tert-butyl esterYield 48.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester (340 mg, 46.2%) was prepared according to the procedure in Example 25 from 6-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (486 mg, 2 mmol) with isobutyl chloroformate (273.16 mg, 2.0 mmol) and triethylamine (1.14 g, 8 mmol) in THF (6 mL). Then 3-cyano-N-hydroxy-benzamidine (306 mg, 1.9 mmol) and DMF (5 mL) were added and the mixture was heated at 130˜135° C. for 3 h. 1H NMR (CDCl3), δ(ppm): 8.38 (d, 1H), 8.32 (dd, 1H), 7.77 (dd, 1H), 7.61 (t, 1H), 5.58 (d, 1H), 4.43 (m, 1H), 2.55 (m, 1H), 1.50–1.98 (m & s, 14H), 0.96 (d, 3H).

Workup

  1. temperaturethe mixture was heated at 130˜135° C. for 3 h

Sources & evidence

ORD record
ord-1699df2f672043e7829a1f11eb94148c
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

Loading…