Hydrochloric Acid → 2-((Ethylaminocarbonyl)amino)-n-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamide

HRID 1825034Notes

Reaction equation

HRID 1825034 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=1)=[O:9])=[O:5].C(N(CC)CC)C.[CH2:43]([N:45]=[C:46]=[O:47])[CH3:44].Cl>C1COCC1.CCOC(C)=O>[CH2:43]([NH:45][C:46]([NH:1][C:2]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=1)=[O:9])=[O:5])=[O:47])[CH3:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 68828834HCID 68828834, compound

Product 1

HCID 101448562-((Ethylaminocarbonyl)amino)-n-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamideYield 17.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(amino)-N-[2-[[(cis)-2-[[4-(methylthio)benzoyl]amino]cyclohexyl]amino]-2-oxoethyl]-5-trifluoromethyl benzamide (Example 114a) (50 mg) was dissolved in THF (2.5 mL) prior to the addition of triethylamine (30 mg) and ethyl isocyanate (21 mg). After stirring for 72 h, EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) provided the title benzamide (10 mg). MS found: (M+Na)+=602.4.

Workup

  1. washThe EtOAc layer was washed with 1 N HCl and brine
  2. dry with materialThe EtOAc was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA)

Sources & evidence

ORD record
ord-ef621d2f8d994e1586caafdcd7c93641
Source dataset
uspto-grants-2006_05
Patent number
US07045521B2

Reaction notes

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