Formic Acid → HCID 136199107, compound

HRID 660911Notes

Reaction equation

HRID 660911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](CC=C)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH2:22]C)=[O:19])[N:9]=2)=[CH:4][CH:3]=1.[CH2:34](N(CC)CC)C.C(O)=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][C:21]([CH3:34])([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)[CH3:22])=[O:19])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 69074369HCID 69074369, compound

Product 1

HCID 136199107HCID 136199107, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
85 °C

Procedure

2.00 g (4.12 mmol) of 2-[3-(4-chlorophenyl)-4-allyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 371 are dissolved in 20 ml degassed dioxan and treated under argon with 97 mg of tetrakis(triphenylphosphine)-palladium(0) (0.084 mmol), 1.46 ml (10.44 mmol) of triethylamine and 0.32 ml (8.35 mmol) of formic acid and stirred for two hours at 85° C. The suspension is then allowed to cool to room temperature and the precipitated crystals are filtered off at the pump and washed with isopropanol. The mother liquor is concentrated in vacuo and treated with isopropanol, during which further crystals deposit, which are likewise suction-filtered and washed with isopropanol. Together 1.56 g (85% of theory) of the target compound are thus obtained.

Workup

  1. customdegassed dioxan
  2. temperatureto cool to room temperature
  3. filtrationthe precipitated crystals are filtered off at the pump
  4. washwashed with isopropanol
  5. concentrationThe mother liquor is concentrated in vacuo
  6. additiontreated with isopropanol, during which further crystals deposit, which
  7. filtrationare likewise suction-filtered
  8. washwashed with isopropanol
  9. customTogether 1.56 g (85% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-30a3d39925b04cdcaab6937e688f7cf2
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

Loading…