Pyridine → (+/-)-N-(2-pyrimidinyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide

HRID 727267Notes

Reaction equation

HRID 727267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[CH:10]([CH2:24][C:25](O)=[O:26])[N:9]=2)=[CH:4][CH:3]=1.[NH2:28][C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1.N1C=CC=CC=1.[Cl-].ClC1N(C)C=C[N+]=1C>ClC(Cl)C>[N:30]1[CH:31]=[CH:32][CH:33]=[N:34][C:29]=1[NH:28][C:25](=[O:26])[CH2:24][CH:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]12

Participants

6

Reactant 4

HCID 1049PyridineHCID 79782-AminopyrimidineHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 197049212-[7-(4-Chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0,2,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetic acid

Product 1

HCID 19704922(+/-)-N-(2-pyrimidinyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

(±)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (1.0 g), 2-aminopyrimidine (0.28 g) and pyridine (0.49 ml) are added to dichloroethane (15 ml), and the mixture is stirred in an ice bath. A solution of 2-chloro-1,3-dimethylimidazolium chloride (0.63 g) in dichloroethane (12 ml) is dropwise added to this mixture at a temperature of not more than 5° C. The mixture is stirred at room temperature overnight, and the reaction mixture is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled away and the residue is purified by column chromatography (chloroform:methanol=20:1) and recrystallized from ethanol to give 0.78 g of (±)-N-(2-pyrimidinyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide, melting point 251°-253° C.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. washthe reaction mixture is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled away
  5. customthe residue is purified by column chromatography (chloroform:methanol=20:1)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-81d3e8f2c1054f46a742673dfc920ba6
Source dataset
uspto-grants-1998_01
Patent number
US05712274

Reaction notes

Loading…