Sodium Carbonate → HCID 16124832, compound

HRID 239884Notes

Reaction equation

HRID 239884 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([N:11]1[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]1=[O:21])=[N:5][NH:6]2.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([N:11]1[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]1=[O:21])=[N:5][N:6]2[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 16125234HCID 16125234, compound

Product 1

HCID 16124832HCID 16124832, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 162A (100 mg), 4-(2-chloroethyl)morpholine (48 mg), and Na2CO3 (82 mg) in DMF (5 mL) was heated overnight at 80° C., cooled to room temperature, and partitioned between 1N HCl and ethyl acetate. The aqueous layer was basified with 1N KOH and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide 45 mg of the desired product. MS (ESI(+)) m/e 503 (M+H)+.

Workup

  1. custompartitioned between 1N HCl and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f9aaec080224eb3b9b8dadd41615033
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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