Morpholine → HCID 58804051, compound

HRID 349279Notes

Reaction equation

HRID 349279 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([C:18]([C:20]2[C:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])=[N:22][O:23][C:24]=2[CH2:25]Cl)=[O:19])[N:9]=[N:8]1.C(N(CC)CC)C.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>ClCCl>[F:38][C:37]([F:39])([F:40])[C:35]1[CH:34]=[C:5]([CH:4]=[C:3]([C:2]([F:41])([F:1])[F:42])[CH:36]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[C:10]([C:18]([C:20]2[C:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])=[N:22][O:23][C:24]=2[CH2:25][N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)=[O:19])[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 58804025HCID 58804025, compound

Product 1

HCID 58804051HCID 58804051, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat a mixture of [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-[5-chloromethyl-3-(2-chloro-phenyl)-isoxazol-4-yl]-methanone (100 mg, 0.158 mmol), triethylamine (80 mg, 0.790 mL) and morpholine (0.79 mL) at 50° C. for 18 h. Cool to RT, dilute the mixture with dichloromethane (50 mL) and wash with water (4×40 mL). Dry the organic layer with anhydrous MgSO4, filter, and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to give the title compound (93% yield) as a brown oil. MS (ES) 685.2 (M++1); TLC Rf=0.1 (75% EtOAc in hexanes).

Workup

  1. temperatureHeat
  2. washwash with water (4×40 mL)
  3. dry with materialDry the organic layer with anhydrous MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1c369a354691454c9ad4aec5bb079391
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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