Water → HCID 15718986, compound

HRID 2166150Notes

Reaction equation

HRID 2166150 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[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][CH2:17]1)[CH3:2].[OH-].[Na+].O>C(O)C>[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[NH:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:20][CH2:21]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15718897HCID 15718897, compound

Product 1

HCID 15718986HCID 15718986, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.5 parts of ethyl 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidineacetate, 15 parts of a sodium hydroxide solution 1N, 100 parts of water and 16 parts of ethanol was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was taken up in water, washed with dichloromethane and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (80:20 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1 part (19.1%) of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidineacetic acid; mp. 227.3° C. (compound 182).

Workup

  1. customThe reaction mixture was evaporated
  2. washwashed with dichloromethane
  3. custompurified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 2-propanol
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-aeec3ce7ef284fb28c1596c26a2d2b68
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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