Sodium Carbonate → HCID 86743150, compound

HRID 1904843Notes

Reaction equation

HRID 1904843 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH2:31])[CH2:25][CH2:24]1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].CN(C)C(=[O:42])C>O>[C:11]([OH:7])(=[O:42])[C:32]([OH:34])=[O:35].[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH:31][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 764302-BromothiazoleHCID 14013481HCID 14013481, compound

Product 1

HCID 86743150HCID 86743150, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3.3 parts of 2-bromothiazole, 5.09 parts of 4[[3-(2-furanylmethy)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineethanamine, 3 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 130° C. The reaction mixture was poured into water and the product was extracted twice with 4-methyl-2-pentanone. 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 2.5 parts (27%) of 4-[[3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-N-(2-thiazolyl)-1-piperidineethanamine ethanedioate (1:3); mp. 173.0° C. (352).

Workup

  1. extractionthe product was extracted twice with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9a3f0bd6fa3f4050935c02d1350dd639
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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