Hydrochloric Acid → 2-(3-Amino-5-methyl-1H-pyrazol-4-YL)-benzothiazole-6-carboxylic acid methyl ester

HRID 407352Notes

Reaction equation

HRID 407352 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[C:5]([CH3:19])[NH:4][N:3]=1.Cl.[CH3:21]O>>[CH3:21][O:17][C:16]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([C:6]3[C:2]([NH2:1])=[N:3][NH:4][C:5]=3[CH3:19])[S:8][C:9]=2[CH:15]=1)=[O:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66768016HCID 66768016, compound

Product 1

HCID 667679822-(3-Amino-5-methyl-1H-pyrazol-4-YL)-benzothiazole-6-carboxylic acid methyl ester

Procedure

A solution of 2-(3-amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-6-carboxylic acid (1.52 g, 5.5 mmol) in 500 mL of anhydrous methanol containing HCl gas was heated to reflux for 5 hrs. The excess methanol was removed by distillation and the solution was neutralized by the addition of a solution of saturated sodium carbonate. The resulting solids were isolated by filtration to yield 500 mg of the title compound as a yellow solid. MS (m/z, ES+): 289.1 (M+1, 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hrs
  3. customThe excess methanol was removed by distillation
  4. additionthe solution was neutralized by the addition of a solution of saturated sodium carbonate
  5. customThe resulting solids were isolated by filtration

Sources & evidence

ORD record
ord-43abfcffd1864aba8ef3e98888657150
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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