4-Fluorobenzylamine → HCID 22346292, compound

HRID 897308Notes

Reaction equation

HRID 897308 reaction equation
C([O:9][C:10]1[C:11]([C:27]([O:29]C)=O)=[N:12][C:13]([O:20][CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=O)C1C=CC=CC=1.[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:27]([C:11]2[C:10]([OH:9])=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[C:13]([O:20][CH2:21][C:22]([N:24]([CH3:25])[CH3:26])=[O:23])[N:12]=2)=[O:29])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 22346259HCID 22346259, compound

Product 1

HCID 22346292HCID 22346292, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl ester from Step 1 (0.28 g, 0.68 mmol) and 4-fluorobenzylamine (0.16 mL, 1.43 mmol) in toluene (5 mL) was heated in an oil bath at 110° C. overnight. The resultant precipitate was filtered, washed with diethyl ether, and dried under vacuum. The solid was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as yellow solid.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with diethyl ether
  3. customdried under vacuum
  4. dissolutionThe solid was dissolved in DMSO
  5. customsubjected to HPLC purification on C-18 stationary phase
  6. washeluted with water/acetonitrile/TFA mobile phase
  7. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-2a9fa19e028040bf8f24c0c3869e98c5
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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