Triethylamine → HCID 59385407, compound

HRID 2356841Notes

Reaction equation

HRID 2356841 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:20](=O)[CH2:21][C:22]#[N:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl.[C:33]([NH:37][NH2:38])([CH3:36])([CH3:35])[CH3:34]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:20]2[CH:21]=[C:22]([NH2:23])[N:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:38]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 59385358HCID 59385358, compound

Product 1

HCID 59385407HCID 59385407, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.66 g (5.0 mmol) of 4-(2-cyanoacetyl)-4-phenylpiperidine-1-carboxylic acid tert-butyl ester, 2.20 mL (16 mmol) of Et3N and 2.00 g (16 mmol) of tert-butylhydrazine hydrochloride in 20 mL of absolute EtOH was heated to 100° C. in a sealed tube. After 64 h, the reaction mixture was cooled to rt and concentrated. Purification on silica gel using 30:70 EtOAc-hexanes as eluant afforded 4-(5-amino-1-tert-butyl-1H-pyrazol-3-yl)-4-phenylpiperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationconcentrated
  2. customPurification on silica gel using 30:70 EtOAc-hexanes as eluant

Sources & evidence

ORD record
ord-ddb198fa0a6644b695db211837ac0636
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

Loading…