HCID 59547946, compound → HCID 59547991, compound

HRID 1946383Notes

Reaction equation

HRID 1946383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][C:19]=2[C:27]([F:30])([F:29])[F:28])[N:13]=1)=[O:10]>C1COCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]([NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2[CH:26]=[CH:25][C:21]([CH2:22][OH:23])=[CH:20][C:19]=2[C:27]([F:28])([F:30])[F:29])[N:13]=1)=[O:10]

Participants

3

Reactant 1

HCID 59547946HCID 59547946, compound

Product 1

HCID 59547991HCID 59547991, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]-3-(trifluoromethyl)benzoic acid (for a preparation see Intermediate 21)(0.340 g, 0.80 mmol) in THF (5 ml) at ambient temperature under nitrogen was added 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol). The solution was stirred at ambient temperature under nitrogen for 1 h. To the suspension was added a further amount of 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol). The solution was stirred for a further 2 h. The solvent was removed in vacuo to leave a colourless gum. The residue was re-dissolved in THF (5 ml). To the solution was added 1.0M boran-tetrahydrofuran complex (2 ml, 2 mmol) and stirred for 6 h. The solution was quenched with methanol (10 ml), stirred for 5 min and then the solvent removed in vacuo. The residue was loaded in dichloromethane and purified on silica (20 g) using 0-100% ethyl acetate-cyclohexane+0-20% methanol. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless gum (0.20 g);

Workup

  1. customat ambient temperature
  2. additionwas added 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol)
  3. additionTo the suspension was added a further amount of 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol)
  4. stirringThe solution was stirred for a further 2 h
  5. customThe solvent was removed in vacuo
  6. customto leave a colourless gum
  7. additionTo the solution was added 1.0M
  8. stirringstirred for 6 h
  9. customThe solution was quenched with methanol (10 ml)
  10. stirringstirred for 5 min
  11. customthe solvent removed in vacuo
  12. custompurified on silica (20 g)
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-5902201023c046b587a63e2256f809fa
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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