Trifluoroacetic acid → HCID 136364260, compound

HRID 1700301Notes

Reaction equation

HRID 1700301 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][CH:16]=[CH:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([C:25](=[NH:27])[NH2:26])[CH:19]=3)=[CH:10][C:9]=2[C:28]([F:31])([F:30])[F:29])[CH2:3][CH2:2]1.[C:32](=O)([O:34]C1C=CC=CC=1)[NH2:33].CCN(CC)CC.FC(F)(F)C(O)=O>CO>[NH2:33][C:32]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][CH:16]=[CH:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([C:25](=[NH:26])[NH2:27])[CH:19]=3)=[CH:10][C:9]=2[C:28]([F:29])([F:30])[F:31])[CH2:3][CH2:2]1)=[O:34]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 69322Phenyl carbamateHCID 136364261HCID 136364261, compound

Product 1

HCID 136364260HCID 136364260, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-(piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-hydroxy-3-amidinophenyl)prop-2-en-1-yl)benzenamine (75 mg) in MeOH was added phenyl carbamate (37 mg) and Et3N (0.073 mL). The reaction mixture was stirred at ambient temperature for 3 hours, acidified with trifluoroacetic acid and purified on HPLC (10-40% acetonitrile in water with 0.1% trifluoroacetic acid). The corresponding peak was collected and freezed dried to afford 4-(N′-(aminocarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-hydroxy-3-amidinophenyl)prop-2-en-1-yl)benzenamine.

Workup

  1. custompurified on HPLC (10-40% acetonitrile in water with 0.1% trifluoroacetic acid)
  2. customThe corresponding peak was collected
  3. customfreezed dried

Sources & evidence

ORD record
ord-b35980990d1f4c629c99c7042d069713
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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