Hydrochloric Acid → HCID 178426025, compound

HRID 1741010Notes

Reaction equation

HRID 1741010 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:16]([S:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][C:36]#[N:37])=[CH:28][CH:27]=2)[NH:15][N:14]=1)(=[O:11])=[O:10].C([Sn]([N:51]=[N+:52]=[N-:53])(CCCC)CCCC)CCC.Cl>C(O)COCCO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:16]([S:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][CH2:35][C:36]3[NH:53][N:52]=[N:51][N:37]=3)=[CH:30][CH:31]=2)[NH:15][N:14]=1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 178426026HCID 178426026, compound

Product 1

HCID 178426025HCID 178426025, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

The 3-(2-methyl-5-fluorophenyl)sulfonylamino-4-(2-pyridyl)-5-(4-(3-cyanopropoxy)benzylthio)-(1H)-pyrazole (0.537 g), prepared as described in Example 7, above, in diethylene glycol was treated with 1.5 equivalents of tributyltin azide and heated at reflux temperature overnight. After cooling, 2N hydrochloric acid (2 ml) was added and the mixture was stirred 1 hr at room temperature. After extraction with tetrahydrofuran, the organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum. Flash chromatography over silica with 3:1 chloroform/ethyl acetate (1 1.), followed by the same solvent plus 5% methanol afforded 0.256 g (44% yield) of the pure product which crystallized from chloroform.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature overnight
  3. temperatureAfter cooling
  4. extractionAfter extraction with tetrahydrofuran
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-34b356d68fb346418aeba8c3f761cfd4
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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