Trimethyl orthoformate → HCID 21912067, compound

HRID 2307995Notes

Reaction equation

HRID 2307995 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[CH:25](OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[CH:25]=[N:24][C:8]=12)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21912102HCID 21912102, compound

Product 1

HCID 21912067HCID 21912067, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(1-ethyl-propoxy)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3-diamine, trimethyl orthoformate, p-toluenesulfonic acid monohydrate in toluene was heated at reflux using Dean-Stark apparatus for 24 hours. The mixture was heated at reflux overnight. The mixture was quenched with water, sat. NaHCO3, extracted with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness. After purification, the title compound was isolated. Anal. For C21H29N3O.¼H2O calc. C, 73.76; H, 8.10; N, 12.29; found: C, 73.22; H, 7.96; N, 12.42.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 24 hours
  4. temperatureThe mixture was heated
  5. temperatureat reflux overnight
  6. customThe mixture was quenched with water, sat. NaHCO3
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated to dryness
  11. customAfter purification

Sources & evidence

ORD record
ord-e6b24538273c46749e933fbbb86829d8
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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