Sodium Carbonate → HCID 131716287, compound

HRID 1084756Notes

Reaction equation

HRID 1084756 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[N:7]([CH2:10][CH3:11])[N:6]=[N:5]1.[CH3:12][C:13]1[O:17][C:16]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[NH:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:15][CH:14]=1.[C:35](=[O:38])([O-:37])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:8]([OH:9])(=[O:17])[C:35]([OH:37])=[O:38].[CH2:10]([N:7]1[C:8](=[O:9])[N:4]([CH2:3][CH2:2][N:32]2[CH2:33][CH2:34][CH:29]([NH:28][C:20]3[N:19]([CH2:18][C:16]4[O:17][C:13]([CH3:12])=[CH:14][CH:15]=4)[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=3)[CH2:30][CH2:31]2)[N:5]=[N:6]1)[CH3:11]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 30199151-(2-Bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-oneHCID 14677561HCID 14677561, compound

Product 1

HCID 131716287HCID 131716287, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.32 parts of 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one, 4.65 parts of 1-[(5-methyl-2-furanyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 1.6 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 80° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in methanol. The salt was filtered off and dried, yielding 5.2 parts (55%) of 1-ethyl-1,4-dihydro-4-[2-[4-[[1-[(5-methyl-2-furanyl)methyl]-1H-benzimidazol-2-yl]-amino]-1-piperidinyl]ethyl]-5H-tetrazol-5-one ethanedioate(1:2); mp. 190.5° C. (compound 22).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe residue was purified by filtration over silica gel using
  6. additiona mixture of trichloromethane and methanol (96:4 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-b581ff6776b84f3f831957344f1e4d24
Source dataset
uspto-grants-1991_04
Patent number
US05006527

Reaction notes

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