Methylamine → HCID 10280886, compound

HRID 1610962Notes

Reaction equation

HRID 1610962 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]4[CH:32]=[CH:31][N:30]=[C:29]4[CH2:33][CH2:34][C:35](OCC)=[O:36])=[CH:20][CH:19]=3)[N:15]=2)=[CH:5][CH:4]=1.[CH3:42][NH2:43]>C(O)C>[CH3:42][NH:43][C:35](=[O:36])[CH2:34][CH2:33][C:29]1[N:28]([CH2:27][CH2:26][CH2:25][CH2:24][C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][C:14]3[N:15]=[C:11](/[CH:10]=[CH:9]/[C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:40])([F:41])[F:1])=[CH:8][CH:7]=4)[O:12][CH:13]=3)=[CH:23][CH:22]=2)[CH:32]=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22259325HCID 22259325, compound

Product 1

HCID 10280886HCID 10280886, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]propionate (180 mg) and a solution (3 ml) of 30% methylamine in ethanol in sealed tube was heated at 120° C. for 12 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=30:1) and recrystallized from ethyl acetate-hexane to give the titled compound (43 mg) as a colorless crystal powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=30:1)
  3. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0203bdd1b4048cabec66f59e4d25fce
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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