HCID 18663201, compound → HCID 18663189, compound

HRID 1956970Notes

Reaction equation

HRID 1956970 reaction equation
[CH3:1][C:2]1[C:3]([N:8](COCCOC)[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:20][C:19]=3[CH2:30][N:31]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[N:32]3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7]>CCO.Cl>[CH3:1][C:2]1[C:3]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:25]=[CH:26][CH:27]=[CH:28][N:29]=4)=[CH:20][C:19]=3[CH2:30][N:31]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[N:32]3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[N:4][O:5][C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 18663201HCID 18663201, compound

Product 1

HCID 18663189HCID 18663189, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To the solution of N-(4,5-dimethyl-3-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)-2'-[[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl][1,1'-biphenyl]-2-sulfonamide in 3 ml of 95% EtOH, 3 ml 6N HCl was added. The mixture was refluxed for 1 hr and concentrated. 10 ml H2O was added and the mixture was extracted with 3×30 ml EtOAc. The combined organic extracts were washed with brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 24% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 76% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (87 mg, 77% for two steps) as a white solid. m.p. 108°-114° C. (amorphous).

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. concentrationconcentrated
  3. addition10 ml H2O was added
  4. extractionthe mixture was extracted with 3×30 ml EtOAc
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-989adc47a8ec4178ac097ebd656b957b
Source dataset
uspto-grants-1998_07
Patent number
US05780473

Reaction notes

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