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Sodium Carbonate → 7-[3-(Dimethylamino)propoxy]-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371931
Notes
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Reaction equation

HRID 371931 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].C([Li])CCC.Cl[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:25])[N:17]=[C:16]2[N:26]([CH3:29])[CH:27]=[N:28][C:15]=12.C(=O)([O-])[O-].[Na+].[Na+]>CCCCCC.C1C=CC=CC=1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:25])[N:17]=[C:16]2[N:26]([CH3:29])[CH:27]=[N:28][C:15]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 766463-(Dimethylamino)-1-propanolHCID 123876407-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl esterHCID 178418339Butyllithium

Product 1

HCID 123876447-[3-(Dimethylamino)propoxy]-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.1 g. of 3-dimethylaminopropan-1-ol in 100 ml. of dry benzene are added 4 ml. of a 20% solution of butyl lithium in hexane. The mixture is stirred at room temperature for 15 minutes. After this time 2.5 g. of 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester are added and the solution is heated at reflux temperature with stirring for 12 hours. After cooling, the solution is shaken with 50 ml. of a saturated aqueous sodium carbonate solution. The benzene layer is separated, dried with calcium chloride and evaporated to dryness. The remaining oily residue, 7-[3-(dimethylamino)propoxy[-3, 5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, is purified by distillation, yield 2.2 g. (85%); b.p. 175°-180°/0.01 mm.

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. stirringwith stirring for 12 hours
  4. temperatureAfter cooling
  5. stirringthe solution is shaken with 50 ml
  6. customThe benzene layer is separated
  7. dry with materialdried with calcium chloride
  8. customevaporated to dryness
  9. distillationThe remaining oily residue, 7-[3-(dimethylamino)propoxy[-3, 5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, is purified by distillation, yield 2.2 g

Sources & evidence

ORD record
ord-6eb54cdca7844479a6ed7f56aef8c9ff
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04088654

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes