Water → HCID 178486840, compound

HRID 1785489Notes

Reaction equation

HRID 1785489 reaction equation
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[N:7]([C:10]3[S:11][C:12]([C:21]#[N:22])=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+].O>CN1CCCC1=O>[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][C:6]2[N:7]([C:10]3[S:11][C:12]([C:21]4[NH:29][N:28]=[N:27][N:22]=4)=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57595856HCID 57595856, compound

Product 1

HCID 178486840HCID 178486840, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carbonitrile (261 mg, 0.72 mmol), sodium azide (220 mg) and ammonium chloride (250 mg) in N-methylpyrrolidone (2.5 ml) was stirred at 110° C. for 1 hr. Water was added and the mixture was extracted with methylene chloride. After removal of solvent, the residue was purified by HPLC to yield the product (138.1 mg, yield 47%). 1H-NMR (DMSO-D6) 8.78 (s, 1H); 8.21-8.29 (m, 2H); 7.86 (s, 1H); 7.36-7.50 (m, 3H); 3.90 (s, 3H); 3.88 (s, 3H). MS M/z 406 (M+1).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. customAfter removal of solvent
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-fb6e880335694781a11645def0a210f7
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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