Acetonitrile → N-(2-methoxycarbonyl-6-methylphenyl)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1165543Notes

Reaction equation

HRID 1165543 reaction equation
C[Si](C)(C)[NH:3][C:4]1[C:5](=[CH:10][CH:11]=[CH:12][C:13]=1[CH3:14])[C:6]([O:8][CH3:9])=[O:7].CC#N.Cl[S:21]([C:24]1[N:34]=[C:27]2[N:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[N:26]2[N:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:4]=1[NH:3][S:21]([C:24]1[N:34]=[C:27]2[N:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[N:26]2[N:25]=1)(=[O:22])=[O:23])=[O:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 14626580methyl N-trimethylsilyl-3-methylanthranilate

Product 1

HCID 14155161N-(2-methoxycarbonyl-6-methylphenyl)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution consisting of 145.9 mg (0.615 mmole) of methyl N-trimethylsilyl-3-methylanthranilate, 1 ml of CH3CN, and 80.4 mg (0.326 mmole) of 2-chlorosulfonyl-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine was stirred at room temperature and the reaction monitored by reverse phase HPLC. The reaction was about 30 percent complete after 4 hours. Pyridine, 29.1 μl (0.360 mmole), was added and the solution stirred for 10 min and again analyzed. Complete reaction had occurred. The solution was allowed to stand overnight. The CH3CN was removed under a nitrogen atmosphere and the residue treated with 2 ml of 1.0N HCl and 2 ml of CH2Cl2. The CH2Cl2 phase was transferred to a column containing 50 g of silica gel and chromatographed to obtain 112.5 mg of N-(2-methoxycarbonyl-6-methylphenyl)-5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide (0.300 mmole, 92.0 percent yield) as a white crystalline solid, m.p. 181°-182° C. The solid was dissolved in CHCl3 and the solvent again removed in vacuo affording the product as a light yellow powder, m.p. 192°-194° C.

Workup

  1. customcomplete after 4 hours
  2. stirringthe solution stirred for 10 min
  3. customComplete reaction
  4. customThe CH3CN was removed under a nitrogen atmosphere
  5. additionthe residue treated with 2 ml of 1.0N HCl and 2 ml of CH2Cl2
  6. additioncontaining 50 g of silica gel
  7. customchromatographed

Sources & evidence

ORD record
ord-a18f26157d1944d0a788d3c6760417f4
Source dataset
uspto-grants-1990_03
Patent number
US04910306

Reaction notes

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