Sodium Carbonate → HCID 67922858, compound

HRID 2248627Notes

Reaction equation

HRID 2248627 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][N:7]([CH2:10][CH3:11])[C:6]1=[O:12].[NH2:13][C:14]1[C:30]([Cl:31])=[CH:29][C:17]([C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]2[O:27][CH3:28])=[O:19])=[C:16]([O:32][CH3:33])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].[K]>CN(C)C(=O)C>[NH2:13][C:14]1[C:30]([Cl:31])=[CH:29][C:17]([C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][N:5]3[CH2:9][CH2:8][N:7]([CH2:10][CH3:11])[C:6]3=[O:12])[CH2:23][C@H:22]2[O:27][CH3:28])=[O:19])=[C:16]([O:32][CH3:33])[CH:15]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 5462222PotassiumHCID 98616214-Amino-5-chloro-2-methoxy-N-[(3R,4S)-3-methoxypiperidin-4-YL]benzamideHCID 15078469HCID 15078469, compound

Product 1

HCID 67922858HCID 67922858, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6.3 parts of 1-(3-chloropropyl)-3-ethyl-2-imidazolidinone, 4.76 parts of cis-4-amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidinyl)benzamide, 2.3 parts of sodium carbonate, 0.1 parts of potassium iode and 90 parts of N,N-dimethylacetamide was stirred over weekend at 70° C. After cooling, the reaction mixture was evaporated. The residue was taken up in dichloromethane and water. The organic layer was separated, washed twice with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile and a few drops of water at 0° C. The product was filtered off and dried in vacuo at 40° C., yielding 2.83 parts (36.6%) of cis-4-amino-5-chloro-N-[1-[3-(3-ethyl-2-oxo-1-imidazolidinyl)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide; mp. 112.9° C. (compound 12).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. customThe organic layer was separated
  4. washwashed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from acetonitrile and a few drops of water at 0° C
  13. filtrationThe product was filtered off
  14. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-4bf41be2c0ef463e9126e4e8e2dd6443
Source dataset
uspto-grants-1991_08
Patent number
US05041454

Reaction notes

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