Sodium Carbonate → HCID 131718800, compound

HRID 52673Notes

Reaction equation

HRID 52673 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[OH2:19].[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36].[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 810792-ChloronicotinonitrileHCID 67704528cis-4-amino-N-[1-(4-aminobutyl)-3-methoxy-4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide

Product 1

HCID 131718800HCID 131718800, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.4 parts of 2-chloro-3-pyridinecarbonitrile, 3.2 parts of cis-4-amino -N-[1-(4-aminobutyl)-3-methoxy-4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide, 65.8 parts of N,N-dimethylformamide and 1.3 parts of sodium carbonate was stirred for 20 hours at 70° C. The solvent was evaporated and the residue was dissolved in trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH (NH3) 98:2). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The product was dried in vacuo at 60° C., yielding 1.44 parts (35.4%) of cis-4-amino-5-chloro-N-[1-[4-[(3-cyano-2-pyridinyl)amino ]butyl]-3-methoxy-4-piperidinyl]-2,3-dihydro-7-benzofurancarboxamide hemihydrate; mp. 129.7° C. (comp. 6).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in trichloromethane
  3. washThe organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH (NH3) 98:2)
  8. customThe eluent of the desired fraction was evaporated
  9. customthe residue was crystallized from 2,2'-oxybispropane
  10. customThe product was dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-739c92f62e44429a97a3a800e5f04d19
Source dataset
uspto-grants-1997_04
Patent number
US05616738

Reaction notes

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