HCID 66613551, compound → HCID 178518777, compound

HRID 510129Notes

Reaction equation

HRID 510129 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=O)[CH:15](O)O)=[N:6]1.S([O:27][C:28]1[NH:32][N:31]=[C:30]([NH2:33])[C:29]=1[NH2:34])(O)(=O)=O>C(O)(=O)C>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[CH:15]=[N:34][C:29]3[C:30](=[N:31][NH:32][C:28]=3[OH:27])[N:33]=2)=[N:6]1

Participants

4

Reactant 2

HCID 66613551HCID 66613551, compoundHCID 178509290HCID 178509290, compound

Product 1

HCID 178518777HCID 178518777, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

500 mg (1.291 mmol) of the compound from example 68A were admixed with 7 ml of acetic acid and 273 mg (1.291 mmol) of 3,4-diamino-1H-pyrazol-5-ol sulfate. The mixture was stirred at RT for 16 h and then concentrated on a rotary evaporator. Water and ethyl acetate were added, and the mixture was stirred. The organic phase was removed and extracted once with a 1N sodium hydroxide solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, ratio 80:15:5). 142 mg of the title compound were obtained (29% of theory).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. additionWater and ethyl acetate were added
  3. stirringthe mixture was stirred
  4. customThe organic phase was removed
  5. extractionextracted once with a 1N sodium hydroxide solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a rotary evaporator
  8. customThe residue was purified by preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, ratio 80:15:5)

Sources & evidence

ORD record
ord-085caec16df646f78bee1df1d4a28c2b
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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