Cyclopentylamine → HCID 178493222, compound

HRID 1857481Notes

Reaction equation

HRID 1857481 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([O:23][CH3:24])[CH:14]=1)OC1C=CC=CC=1)#[N:2].[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C>C(#N)C>[C:1]([NH:3][C:4]([NH:30][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=[N:12][C:13]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[C:15]([O:23][CH3:24])[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 11404888HCID 11404888, compound

Product 1

HCID 178493222HCID 178493222, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N-Cyano-N'-(3-methoxy-5-trifluoromethyl-phenyl)-O-phenylisourea (0.52 mmol, 175 mg) in dry acetonitrile (1 ml), cyclopentylamine (1.04 mmol, 0.113 ml) and triethylamine (0.080 ml) were added. The mixture was stirred for 19 h at 75° C. under nitrogen. After concentration the residue was dissolved in dichloromethane, washed with 1 N aqueous HCl (2×), water, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (ethyl acetate/heptane 1:2) to give a syrup. Crystallisation from ethyl acetate/heptane 1:4 gave grey crystals (110 mg, 65%). Mp 101-102° C.; 1H-NMR (CDCl3): δ 1.40 (m, 2H), 1.65 (m, 4H), 2.02 (m, 2H), 4.13 (sextet, 1H), 5.05 (br, 1H), 6.96 (s, 1H), 7.00 (s, 1H), 7.03 (s, 1H), 8.15 ppm (br, 1H); EI SP/MS: 326 (M+).

Workup

  1. concentrationAfter concentration the residue
  2. dissolutionwas dissolved in dichloromethane
  3. washwashed with 1 N aqueous HCl (2×), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (ethyl acetate/heptane 1:2)
  7. customto give a syrup
  8. customCrystallisation from ethyl acetate/heptane 1:4

Sources & evidence

ORD record
ord-78eea1aab5154b3c913fd66c7e5d3617
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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