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Trimethyl orthoacetate → tert-butyl 2-[2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethylcarbamate

HRID 1245922
Notes
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Reaction equation

HRID 1245922 reaction equation
[C:1](OC)(OC)(OC)[CH3:2].[NH2:9][C:10]1[C:11]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:12][C:13]([CH3:31])=[C:14]([CH3:30])[C:15]=1[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:15]2[C:14]([CH3:30])=[C:13]([CH3:31])[N:12]=[C:11]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:10]=2[N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 21913447Tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate

Product 1

HCID 21914077tert-butyl 2-[2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethylcarbamateYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

Trimethyl orthoacetate (3.55 mL, 28.27 mmol), tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate (11.21 g, 26.92 mmol), pyridine hydrochloride (1.12 g) and toluene (120 mL) were combined and heated at reflux for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with water (3×100 mL) and brine (1×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 9.85 g of tert-butyl 2-[2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethylcarbamate.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. washwashed with water (3×100 mL) and brine (1×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce6d3897ebaf4e32ae1730a05d6d02fc
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07125890B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes