Sodium Carbonate → HCID 178526024, compound

HRID 1533959Notes

Reaction equation

HRID 1533959 reaction equation
C([O:3][CH2:4]C[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1CCCCN1CCNCC1)C.ClCC1N(CC[O:38]CC)C2=NC=CC=C2N=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].[N:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 178526024HCID 178526024, compound

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-7614a28c528144eeba0be15c527b1ddc
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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