Hydrochloric Acid → HCID 70865033, compound

HRID 336211Notes

Reaction equation

HRID 336211 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:18][O:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:18][O:17][CH2:16][CH2:15][N:14]2[S:27]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70865354HCID 70865354, compound

Product 1

HCID 70865033HCID 70865033, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of morpholine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (55 mg; 0.19 mmol) in anhydrous DMF (1 mL) is added 4-chlorobenzenesulfonyl chloride (40.1 mg; 0.19 mmol) and N,N-diisopropylethylamine (0.089 mL; 0.513 mmol). The reaction mixture is left stirring at room temperature for 18 hours in the presence of catalytic amount of 4-dimethylaminopyridine. After this time, the reaction mixture is diluted with ethyl acetate and washed with eater 3 times, then brine, dried over Na2SO4, filtered and concentrated in vacuo. Recrystallization from hot methanol provides the title compound, m/z 428 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. washwashed with eater 3 times
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from hot methanol

Sources & evidence

ORD record
ord-b93c5d72406047659012f7e885ced1f9
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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