Sodium Carbonate → HCID 131716832, compound

HRID 1085862Notes

Reaction equation

HRID 1085862 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH3:2].Cl[CH2:26][C:27]1[N:35]([CH2:36][CH2:37][O:38][CH2:39][CH3:40])[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[N:28]=1.[C:41](=[O:44])([O-:43])[O-].[Na+].[Na+]>CN(C)C(=O)C>[C:4]([OH:3])(=[O:38])[C:41]([OH:43])=[O:44].[CH2:39]([O:38][CH2:37][CH2:36][N:35]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[N:28]=[C:27]1[CH2:26][N:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][CH2:15][C:7]2[N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)[CH2:24][CH2:23]1)[CH3:40]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 19911510HCID 19911510, compoundHCID 19911577HCID 19911577, compound

Product 1

HCID 131716832HCID 131716832, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.3 parts of 3-(2-ethoxyethyl)-2-[4-(1-piperazinyl)butyl]-3H-imidazo[4,5-b]pyridine, 2.9 parts of 2-(chloromethyl)-3-(2-ethoxyethyl) -3H-imidazo[4,5-b]pyridine, 1.2 parts of sodium carbonate and 22.5 parts of N,N-dimethylacetamide was stirred for 6 hours at 70° C. The reaction mixture was evaporated and the residue was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanol. The salt was filtered off and crystallized from 2-propanol. The product was filtered off and dried, yielding 0.7 parts (6.8%) of 3-(2-ethoxyethyl)-2-[[4-[4-[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]butyl]-1-piperazinyl]methyl]-3H-imidazo[4,5-b]pyridine ethanedioate(1:6); mp. 121.9° C. (compound 24).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionthe residue was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. filtrationThe salt was filtered off
  7. customcrystallized from 2-propanol
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-e74d1a812ab2400eabda440c5a509d55
Source dataset
uspto-grants-1991_04
Patent number
US05011842

Reaction notes

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