Hydrochloric Acid → HCID 58563764, compound

HRID 336207Notes

Reaction equation

HRID 336207 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[O:18][CH2:17][CH2:16][N:15]([C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([C:21]([F:20])([F:31])[F:32])=[CH:23][CH:24]=3)[CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 99664-(Trifluoromethyl)benzoic acidHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 58563909HCID 58563909, compound

Product 1

HCID 58563764HCID 58563764, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cold (0° C.) solution of morpholine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (75 mg; 0.259 mmol), 4-(trifluoromethyl)benzoic acid (49.2 mg; 0.259 mmol) and N,N-diisopropylethylamine (0.099 mL; 0.57 mmol) in anhydrous acetonitrile (2 mL) is added phosphorous oxychloride (0.023 mL; 0.259 mmol). The reaction mixture is left stirring at room temperature for 3.5 hours. After this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/methylene chloride then trituation from hot methanol provides the title compound, m/z 426 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. customAfter this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with ethyl acetate twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-32e5165a5d8946f0a7f12926f0ca39b5
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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