Triethylamine → HCID 9799262, compound

HRID 1857466Notes

Reaction equation

HRID 1857466 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[N:22][C:23]#[N:24])OC2C=CC=CC=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:27][CH:28]([CH3:32])[CH:29]([NH2:31])[CH3:30].C(N(CC)CC)C>C(#N)C>[C:23]([NH:22][C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=[C:3]([C:2]([F:1])([F:26])[F:25])[CH:4]=1)=[N:31][CH:29]([CH3:30])[CH:28]([CH3:32])[CH3:27])#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117311,2-DimethylpropylamineHCID 178512266HCID 178512266, compound

Product 1

HCID 9799262HCID 9799262, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[3,5-bis(trifluoromethyl)phenyl]-N'-cyano-O-phenylisourea (0.8 mmol, 300 mg), 3-methyl-2-butylamine (0.88 mmol, 0.101 ml) and triethylamine (0.88 mmol, 0.123 ml) in acetonitrile (2 ml) was stirred for 7 h at 75° C. After concentration the residue was dissolved in ethyl acetate, washed with water, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (heptane:ethyl acetate 4:1) to give the title compound (143 mg, 59%) as white crystals. Mp 134-136° C.; EI SP/MS: 366 (M+); 1H-NMR (CDCl3): δ 0.92 (d, 6H),1.15 (d, 3H), 1.78 (m, 1H), 3.78 (m, 1H), 4.85 (br, 1H), 7.73 (br s, 3H), 8.0 ppm (br, 1H); MA calc for C15H16F6N4 :C, 49.18%; H, 4.40%; N, 15.29%. Found: C, 48.95%; H, 4.38%; N 15.08%.

Workup

  1. concentrationAfter concentration the residue
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (heptane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-dbb96d4c33434c778e70dd328edecd85
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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