Ethylmorpholine → HCID 22558362, compound

HRID 984442Notes

Reaction equation

HRID 984442 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:19][C:20](=[O:34])[C:21]([NH:23][C:24]([CH3:33])([CH3:32])[CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:22])[CH:11]=[CH:12][C:13]=1[C:14]1[O:18][CH:17]=[N:16][CH:15]=1.C(N1CCOCC1)C>ClCCl.C(OCC)(=O)C>[CH3:1][S:2]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:25][C:24]([NH:23][C:21](=[O:22])[C:20]([NH:19][C:10]2[CH:11]=[CH:12][C:13]([C:14]3[O:18][CH:17]=[N:16][CH:15]=3)=[C:8]([O:7][CH3:6])[CH:9]=2)=[O:34])([CH3:33])[CH3:32])[CH2:27][CH2:28]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 7525EthylmorpholineHCID 31297Methanesulfonyl chlorideHCID 22558433HCID 22558433, compound

Product 1

HCID 22558362HCID 22558362, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

14 mg (0.12 mmol) of methanesulphonyl chloride were added to a solution of 40 mg (0.1 mmol) of N-[3-methoxy-4-(5-oxazolyl)phenyl-N′-[1,1-dimethyl-2-(4-piperidinyl)ethyl]oxalamide in 1 ml of dichloromethane followed by 17 mg (0.15 mmol) of N-ethylmorpholine and the mixture stirred at room temperature for 4 hours. The resulting solution was diluted with ethyl acetate, washed with 2M hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate, evaporated to dryness and the residue triturated with diethyl ether. There was obtained 23 mg of N-[2-[1-(methanesulfonyl)-4-piperidinyl]-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as an off-white solid. MS m/e 479 [M+H]+.

Workup

  1. washwashed with 2M hydrochloric acid and saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. customevaporated to dryness
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-426adde061b340cab317d568290a76c8
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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