4-Methylmorpholine → HCID 69204935, compound

HRID 748775Notes

Reaction equation

HRID 748775 reaction equation
CN1CCOCC1.Cl.[C:9]([Cl:17])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.Cl.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH:29]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[F:41])[CH2:30][CH2:31][CH2:32][NH2:33])(=[O:28])=[O:27])=[CH:22][CH:21]=1.CCCCCC>ClCCl.C(O)C.C(OCC)(=O)C>[ClH:17].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([CH:29]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[F:41])[CH2:30][CH2:31][CH2:32][NH:33][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8058HexaneHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 69202069HCID 69202069, compound

Product 1

HCID 69204935HCID 69204935, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21584252Ethanol ethylacetateSolvent

Procedure

Under a nitrogen atmosphere and 0° C., N-methylmorpholine (44.6 μl, 0.406 mmol) and nicotinic acid chloride hydrochloride (36.1 mg, 0.203 mmol) were added to a dichloromethane solution (4 ml) of 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)butylamine hydrochloride (67.0 mg, 0.169 mmol). After stirring at room temperature for 3 hours, the reaction mixture was diluted with dichloromethane, washed successively with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:3 eluate was concentrated. The resulting solid was dissolved in ethanol. To the resulting solution was added 1N hydrochloric acid-ethanol (0.5 ml), followed by concentration. The solid thus obtained was recrystallized from ethanol-ethyl acetate, whereby the title compound (67.1 mg, 0.134 mmol, 79%) was obtained as a white solid.

Workup

  1. washwashed successively with a saturated aqueous solution of ammonium chloride, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=1:3 eluate was concentrated
  6. dissolutionThe resulting solid was dissolved in ethanol
  7. additionTo the resulting solution was added 1N hydrochloric acid-ethanol (0.5 ml)
  8. concentrationfollowed by concentration
  9. customThe solid thus obtained

Sources & evidence

ORD record
ord-ab421b86b3f74e08966d6c2b44433f52
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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