Sodium Carbonate → HCID 86745286, compound

HRID 1460531Notes

Reaction equation

HRID 1460531 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:5](=[O:14])[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[N:23]=[C:22]1[NH:30][CH:31]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[C:38](=[O:41])([O-:40])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:5]([OH:14])(=[O:6])[C:38]([OH:40])=[O:41].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][N:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[N:23]=[C:22]1[NH:30][CH:31]1[CH2:37][CH2:36][CH2:35][N:34]([CH2:2][CH2:3][C:4]2[C:5](=[O:14])[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[CH:9]=2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 2641213-(2-Bromoethyl)-2H-1-benzopyran-2-oneHCID 15037375HCID 15037375, compound

Product 1

HCID 86745286HCID 86745286, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.8 parts of 3-(2-bromoethyl)-2H-1-benzopyran-2-one, 4.7 parts of 3-(2-furanylmethyl)-N-(hexahydro-1H-azepin-4-yl)-3H-imidazo[4,5-b]pyridin-2-amine, 1.5 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred for 48 hours at 80° C. After cooling, the reaction mixture was poured into water and the product was extracted with trichloromethane. The extract was 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 pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol. The salt was filtered off and dried, yielding 1 part (10%) of 3-[2-[4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]hexahydro-1H-azepin-1-yl]ethyl]-2H-1-benzopyran-2-one ethanedioate(1:2 ); mp. 179.7° C. (compound 109).

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. filtrationThe salt was filtered off
  11. customdried

Sources & evidence

ORD record
ord-1e88d6e6f9e54b06a91575bc71ae3d02
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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