Sodium Carbonate → HCID 131716477, compound

HRID 2166140Notes

Reaction equation

HRID 2166140 reaction equation
Br[C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[N:26]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[N:19]=2)[CH2:13][CH2:12]1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].CN(C)C(=[O:42])C>O>[C:30]([OH:29])(=[O:42])[C:32]([OH:34])=[O:35].[CH2:30]([O:29][CH2:28][CH2:27][N:26]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[N:19]=[C:18]1[NH:17][CH:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:2]2[S:3][C:4]([CH3:7])=[N:5][N:6]=2)[CH2:12][CH2:13]1)[CH3:31]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 71719042-Bromo-5-methyl-1,3,4-thiadiazoleHCID 15718930HCID 15718930, compound

Product 1

HCID 131716477HCID 131716477, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2.4 parts of 2-bromo-5-methyl-1,3,4-thiadiazole, 5 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-amine, 1.6 parts of sodium carbonate and 47 parts of N,N-dimethylacetamide was stirred overnight at 120° 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, (97:3 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 1.23 parts (13.2%) of 3-(2-ethoxyethyl)-N-[1-[2-[(5-methyl-1,3,4-thiadiazol-2-yl)amino]ethyl]-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate(1:2), hemihydrate; mp. 197.3° C. (compound 129). In a similar manner there is also prepared:

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-f2b52bbdad7f40c2b3e7d6f79a2f3e2a
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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