2-(Ethylamino)ethanol → HCID 49819423, compound

HRID 661275Notes

Reaction equation

HRID 661275 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.[CH2:31]([NH:33][CH2:34][CH2:35][OH:36])[CH3:32]>C(O)C>[CH2:31]([N:33]([CH2:34][CH2:35][OH:36])[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)[CH3:32]

Participants

4

Reactant 2

HCID 80722-(Ethylamino)ethanol2×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 49819423HCID 49819423, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 150 mg (0.337 mmol) of the oxadiazole from Example 23A in 2.25 ml of ethanol were added 601 mg (6.74 mmol) of 2-(ethylamino)ethanol, and then the reaction mixture was stirred in the microwave at 80 for 2 h. Another 601 mg (6.74 mmol) of 2-(ethylamino)ethanol were added and the mixture was stirred in the microwave at 100 for a further 7 h. The solvent was removed under reduced pressure and the crude product was purified by means of preparative HPLC. Yield: 28.3 mg (17% of theory)

Workup

  1. stirringthe mixture was stirred in the microwave at 100 for a further 7 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-d98a66707e0742c1af2d99eff3ee3435
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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