Trifluoroacetic acid → HCID 136364258, compound

HRID 1700300Notes

Reaction equation

HRID 1700300 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:28]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[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:35]([F:38])([F:37])[F:36])[CH2:3][CH2:2]1.[C:39](=[NH:44])(OCC)[CH3:40].C(N(CC)CC)C.FC(F)(F)C(O)=O>C(O)C>[NH:44]=[C:39]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:28]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[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:35]([F:36])([F:37])[F:38])[CH2:3][CH2:2]1)[CH3:40]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 65066Ethyl acetimidateHCID 136364259HCID 136364259, compound

Product 1

HCID 136364258HCID 136364258, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-(piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(carboxy)ethylcarbonyl)-N-(3-(6-(hydroxy)-3-amidinophenyl)prop-2-en-1-yl)benzenamine (2.5 g) and ethyl acetimidate (2 g) in ethanol (100 mL) was added triethylamine and the solution was stirred at ambient temperature for 4 hours. The solution was acidified with trifluoroacetic acid, concentrated, separated on HPLC (CH3CN/H2O, gradient) and freeze-dried to afford 4-(N′-(1-iminoethyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(carboxy)ethylcarbonyl)-N-(3-(6-(hydroxy)-3-amidinophenyl)prop-2-en-1-yl)benzenamine.

Workup

  1. concentrationconcentrated
  2. customseparated on HPLC (CH3CN/H2O, gradient)
  3. customfreeze-dried

Sources & evidence

ORD record
ord-0db0a5c9c3874b65bca50729e2301be3
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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