Hydrochloric Acid → HCID 11495507, compound

HRID 2192197Notes

Reaction equation

HRID 2192197 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:20])[C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[C:18]([Cl:19])[C:11]=12)[NH2:5].[Cl:21][C:22]1[CH:27]=[C:26](Cl)[N:25]=[C:24]([NH2:29])[N:23]=1.Cl.[OH-].[Na+]>O.C(O)C>[Cl:21][C:22]1[N:23]=[C:24]([NH2:29])[N:25]=[C:26]([NH:5][C:4]2[CH:6]=[C:7]([F:20])[C:8]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:16][CH:17]=[C:18]([Cl:19])[C:11]=34)=[C:2]([F:1])[CH:3]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 59740987HCID 59740987, compound

Product 1

HCID 11495507HCID 11495507, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

162 mg (0.55 mmol) of 3,5-difluoro-4-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline and 90 mg (0.55 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 6 ml of water/ethanol 1:1. 56 μl (0.65 mmol) of 37% strength hydrochloric acid are added, and the mixture is heated at reflux for 3 h. Using 1N aqueous sodium hydroxide solution, the pH is adjusted to 7, and the mixture is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is purified by preparative HPLC.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 3 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c8e951473baa4d8bb466c32b598b605f
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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