Triethylamine → HCID 178493323, compound

HRID 1749134Notes

Reaction equation

HRID 1749134 reaction equation
[C:1]([N:3]=[S:4]([C:7]1[C:8]([O:20][CH3:21])=[C:9]([CH:13]=[CH:14][C:15]=1[C:16]([F:19])([F:18])[F:17])[C:10]([OH:12])=O)([CH3:6])=[O:5])#[N:2].[OH:22][C:23]1[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[C-]#N.[K+]>ClCCl.C(#N)C>[OH:22][C:23]1[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[C:24]=1[C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([C:16]([F:17])([F:18])[F:19])=[C:7]([S:4]([CH3:6])(=[N:3][C:1]#[N:2])=[O:5])[C:8]=1[O:20][CH3:21]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 897668943-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluormethyl)benzoic acidHCID 178429390HCID 178429390, compound

Product 1

HCID 178493323HCID 178493323, compoundYield 19.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

165 mg (75% by weight; 0.384 mmol) of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluormethyl)benzoic acid and 68.9 mg (0.614 mmol) of 5-hydroxy-1,3-dimethylpyrazole were initially charged in 20 ml of dichlormethane, and 128 mg (0.666 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. The mixture was stirred at RT for 16 h and, for work-up, washed with 1 M hydrochloric acid. After phase separation, the organic phase was dried, filtered and freed from the solvent on a rotary evaporator. The residue was purified chromatographically and the intermediate obtained was then dissolved in 15 ml of acetonitrile. 104 mg (1.02 mmol) of triethylamine, eight drops of trimethylcyanide and a spatula tip of potassium cyanide were then added. The mixture was stirred at RT for 16 h and, for work-up, freed from the solvent. The residue was taken up in dichloromethane and washed with 3 ml of 1M hydrochloric acid. After phase separation, the organic phase was freed from the solvent and the residue was purified chromatographically, which gave 31.3 mg of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoyl]pyrazole in a purity of 85% by weight.

Workup

  1. washwashed with 1 M hydrochloric acid
  2. customAfter phase separation
  3. customthe organic phase was dried
  4. filtrationfiltered
  5. customfreed from the solvent on a rotary evaporator
  6. customThe residue was purified chromatographically
  7. customthe intermediate obtained
  8. stirringThe mixture was stirred at RT for 16 h and, for work-up
  9. washwashed with 3 ml of 1M hydrochloric acid
  10. customAfter phase separation
  11. customthe residue was purified chromatographically

Sources & evidence

ORD record
ord-d6a49e44eebd46648dbac2a0d8406ee3
Source dataset
uspto-grants-2015_10
Patent number
US09156784B2

Reaction notes

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