Isopropylamine → {3-[3-(Isopropylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

HRID 661267Notes

Reaction equation

HRID 661267 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1.[CH:31]([NH2:34])([CH3:33])[CH3:32]>C(O)C>[CH:31]([NH:34][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[CH2:8]2)[O:4][N:3]=1)([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 58116540{3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone

Product 1

HCID 49819152{3-[3-(Isopropylamino)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}-(morpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 mg (0.225 mmol) of the oxadiazole from Example 23A in 1.5 ml of ethanol were added 266 mg (4.50 mmol) of isopropylamine, and then the reaction mixture was stirred in the microwave at 80 for 2 h. Another 266 mg (4.50 mmol) of isopropylamine were added and the mixture was stirred in the microwave at 80° C. for a further 2 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 69.0 mg (66% of theory)

Workup

  1. stirringthe mixture was stirred in the microwave at 80° C. for a further 2 h
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-fda282d5e5a14fc4a465a00c4f99b650
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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