HCID 178429713, compound → HCID 178429714, compound

HRID 1755927Notes

Reaction equation

HRID 1755927 reaction equation
[SH:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][NH:12][C:13]([C:15]3[CH:35]=[CH:34][C:18]4[O:19]C(C5C=CC=CC=5)(C5C=CC=CC=5)[O:21][C:17]=4[CH:16]=3)=[O:14])[N:10]=[C:6]2[N:5]=[C:4]([CH3:36])[CH:3]=1>FC(F)(F)C(O)=O.O>[OH:21][C:17]1[CH:16]=[C:15]([CH:35]=[CH:34][C:18]=1[OH:19])[C:13]([NH:12][CH2:11][C:9]1[N:10]=[C:6]2[N:5]=[C:4]([CH3:36])[CH:3]=[C:2]([SH:1])[N:7]2[N:8]=1)=[O:14]

Participants

4

Reactant 1

HCID 178429713HCID 178429713, compound

Product 1

HCID 178429714HCID 178429714, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-[(7-Mercapto-5-methyl-s-triazolo[1,5-a]-pyrimidin-2-yl)methyl]-2,2-diphenyl-1,3-benzodioxol-5-carboxamide (22.7 g) are stirred for 1 hour in 210 ml of trifluoroacetic acid and 5 ml of water. A small amount of insoluble material is filtered off and the mother liquor is evaporated to dryness. The yellow residue is treated with 900 ml of ethyl acetate, stirred in an ultrasound bath for 1 hour and subsequently cooled in an ice bath. The yellow solid is filtered off and dried in a vacuum at 40° C. There are obtained 14.4 g of 3,4-dihydroxy-N-(7-mercapto-5-methyl[1.2.4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-benzamide as a yellow powder.

Workup

  1. filtrationA small amount of insoluble material is filtered off
  2. customthe mother liquor is evaporated to dryness
  3. additionThe yellow residue is treated with 900 ml of ethyl acetate
  4. temperaturesubsequently cooled in an ice bath
  5. filtrationThe yellow solid is filtered off
  6. customdried in a vacuum at 40° C

Sources & evidence

ORD record
ord-569a1141dc724b7fae7bad53dbca3ada
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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