Triethylamine → HCID 16100322, compound

HRID 1633907Notes

Reaction equation

HRID 1633907 reaction equation
C1(O[C:8](=[O:24])[NH:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)C=CC=CC=1.[CH3:25][O:26][C:27](=[O:51])[CH2:28][CH2:29][NH:30][C:31](=[O:50])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH:39][CH:40]2[CH2:45][CH2:44][CH:43]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:42][CH2:41]2)=[CH:34][CH:33]=1.FC(F)(F)C([O-])=O.C(N(CC)CC)C>ClCCl.C1(C)C=CC=CC=1>[CH3:25][O:26][C:27](=[O:51])[CH2:28][CH2:29][NH:30][C:31](=[O:50])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][N:39]([CH:40]2[CH2:41][CH2:42][CH:43]([C:46]([CH3:47])([CH3:48])[CH3:49])[CH2:44][CH2:45]2)[C:8]([NH:9][C:10]2[CH:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:21])[F:22])[CH:11]=2)=[O:24])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 84468TrifluoroacetateHCID 16100294HCID 16100294, compoundHCID 16100340Phenyl [3,5-bis(trifluoromethyl)phenyl]carbamate

Product 1

HCID 16100322HCID 16100322, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The above carbamic acid phenyl ester (1.0 g, 2.9 mmol) was mixed with 3-{4-[(4-tert-butyl-cyclohexylamino)methyl]benzoylamino}propionic acid methyl ester, trifluoroacetate (1.07 g, 2.9 mmol), prepared as described above and triethylamine (1.2 mL, 8.6 mmol) in dichloromethane (55 mL) and the resulting mixture was refluxed for 4 hours. The cooled reaction mixture was diluted with toluene (50 mL) and washed with water (3×50 mL) and a mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL), dried (MgSO4) and concentrated in vacuo to afford 1.2 g (67%) of 3-{4-[3-(3,5-bis-trifluoromethylphenyl)-1-(4-tert-butyl-cyclohexyl)ureidomethyl]benzoylamino}propionic acid methyl ester as a solid.

Workup

  1. customprepared
  2. temperaturethe resulting mixture was refluxed for 4 hours
  3. customThe cooled reaction mixture
  4. washwashed with water (3×50 mL)
  5. additiona mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72ea8f845e0a411f91d3775e4f2362c3
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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