HCID 760156, compound → HCID 57475451, compound

HRID 911579Notes

Reaction equation

HRID 911579 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C:7]1[CH:15]=[CH:14][C:10]2[N:11]=[N:12][S:13][C:9]=2[CH:8]=1)=O>CO>[OH:4][CH2:5][C:7]1[CH:15]=[CH:14][C:10]2[N:11]=[N:12][S:13][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 760156HCID 760156, compoundHCID 4311764Sodium borohydride

Product 1

HCID 57475451HCID 57475451, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (1.35 g, 36 mmol) in five portions over 4 h to a solution of benzo[1,2,3]thiadiazole-6-carboxylic acid methyl ester (0.35 g, 1.8 mmol, prepared by following the procedure described in J. Heterocyclic Chem. 1972, 1149) in methanol (18 mL) at 0° C. Add acetone to quench and evaporate the mixture onto silica gel. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 2:3 gradient) to give the desired intermediate (133 mg, 45%). MS (GCMS) m/z: 166 M+.

Workup

  1. customprepared
  2. customat 0° C
  3. customAdd acetone to quench
  4. customevaporate the mixture onto silica gel
  5. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 2:3 gradient)

Sources & evidence

ORD record
ord-d799fbc713344d75b211df4457685cee
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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