Triethylamine hydrochloride → HCID 49764059, compound

HRID 1893245Notes

Reaction equation

HRID 1893245 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:19][CH:18]([NH:20][C:21]([CH2:23][NH:24][C:25](=[O:36])[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)=[O:22])[CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:2].[N-:37]=[N+:38]=[N-:39].[Na+].N(CC)(CC)CC.Cl>O1CCOCC1>[N:2]1[NH:37][N:38]=[N:39][C:1]=1[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:19][CH:18]([NH:20][C:21]([CH2:23][NH:24][C:25](=[O:36])[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=4)=[O:22])[CH2:17]3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 49764057HCID 49764057, compound

Product 1

HCID 49764059HCID 49764059, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-({1-[4-(4-cyanomethyl-phenyl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in Example 21, 250 mg, 0.50 mmol), sodium azide (Aldrich, 160 mg, 2.50 mmol), and Et3N HCl salt (350 mg, 2.50 mmol) in dioxane (5 mL) was heated in a sealed tube to 120° C. overnight. The solvent was removed in vacuo and the residue was purified on a silica gel column using a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-66daab7cebf6435480775fd81962ea86
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

Loading…