Sodium Carbonate → HCID 67915807, compound

HRID 654181Notes

Reaction equation

HRID 654181 reaction equation
[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][C@H:10]2[O:20][CH3:21])=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1.Cl[C:28]1[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[OH2:7].[NH2:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:28]3[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[CH:30][N:29]=3)[CH2:11][C@H:10]2[O:20][CH3:21])=[O:7])=[C:4]([O:25][CH3:26])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 810792-ChloronicotinonitrileHCID 14854956HCID 14854956, compound

Product 1

HCID 67915807HCID 67915807, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.78 parts of cis-4-amino-N-[1-(4-aminobutyl)-3-methoxy-4-piperidinyl]-5-chloro-2-methoxybenzamide, 1.66 parts of 2-chloro-3-pyridinecarbonitrile, 1.58 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred for 24 hours at 70° C. The reaction mixture was evaporated. The residue was taken up in water and the product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The first fraction was collected and the eluent was evaporated. The residue was taken up in acetonitrile. The product was filtered off and dried, yielding 1.12 parts (23%) of cis-4-amino-5-chloro-N-[1-[4-[(3-cyano-2-pyrdinyl)amino]butyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide monohydrate; mp. 103.4° C. (compound 40).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionthe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe first fraction was collected
  10. customthe eluent was evaporated
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-aa7c57b4412c49dbb6aec9e49d2cc973
Source dataset
uspto-grants-1992_07
Patent number
US05130312

Reaction notes

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