Succinic Acid → HCID 21108213, compound

HRID 1766025Notes

Reaction equation

HRID 1766025 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:16]([N:19]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]2[O:33][CH2:32][CH2:31][NH:30][C:29]=2[CH:34]=1)[CH2:20][CH2:21][CH3:22])[CH2:17][CH3:18].C(N(CC)CC)C.[C:42]([OH:49])(=[O:48])[CH2:43][CH2:44][C:45]([OH:47])=[O:46]>C(#N)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O>[C:42]([OH:49])(=[O:48])[CH2:43][CH2:44][C:45]([OH:47])=[O:46].[CH2:16]([N:19]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]2[O:33][CH2:32][CH2:31][N:30]([S:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)(=[O:13])=[O:12])[C:29]=2[CH:34]=1)[CH2:20][CH2:21][CH3:22])[CH2:17][CH3:18]

Participants

9

Reactant 4

HCID 1110Succinic AcidHCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chlorideHCID 17848893HCID 17848893, compound

Product 1

HCID 21108213HCID 21108213, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-naphthalenesulfonyl chloride (388 mg, 1.72 mmol) in acetonitrile (5 ml) was added to a solution of 3,4-dihydro-6-[2-(N,N-propylamino)ethyl]-2H-1,4-benzoxazine hydrochloride (300 mg, 1.14 mmol) obtained in Example 134, 4-dimethylaminopyridine (140 mg, 1.14 mmol) and triethylamine (0.48 ml, 3.43 mmol) in acetonitrile (15 ml) under cooling with ice-bath, and the mixture was stirred at room temperature for 4 hours. Water (50 ml) was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with 10% aqueous potassium carbonate and a saturated saline solution, dried over anhydrous sodium sulfate and concentrated. The residues were purified by silica gel column chromatography (developing solvent; ethyl acetate), and succinic acid (1 equivalent) was added thereto, and the product was recrystallized from ethyl acetate-diisopropyl ether, whereby the title compound (220 mg) was obtained as crystals with a mp of 144 to 145° C.

Workup

  1. temperatureunder cooling with ice-bath
  2. extractionwas then extracted with ethyl acetate
  3. washThe extract was washed with 10% aqueous potassium carbonate
  4. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionwas added
  7. customthe product was recrystallized from ethyl acetate-diisopropyl ether, whereby the title compound (220 mg)
  8. customwas obtained as crystals with a mp of 144 to 145° C.

Sources & evidence

ORD record
ord-13b92da7f00a4b44ad8d7e63d5084369
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

Loading…