Hydrochloric Acid → HCID 11660878, compound

HRID 2192195Notes

Reaction equation

HRID 2192195 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]([F:20])[C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=23)=[C:4]([F:21])[CH:3]=1.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[N:24]=1.Cl.[OH-].[Na+]>O.C(O)C>[NH2:29][C:25]1[N:26]=[C:27]([NH:1][C:2]2[CH:19]=[C:18]([F:20])[C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=34)=[C:4]([F:21])[CH:3]=2)[CH:28]=[CH:23][N:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2233322-Amino-4-chloropyrimidineHCID 59740983HCID 59740983, compound

Product 1

HCID 11660878HCID 11660878, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

250 mg (0.65 mmol) of 4-(4-amino-2,6-difluorophenoxy)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile and 92 mg (0.71 mmol) of 4-chloropyrimidine-2-amine are suspended in 10 ml of water and 5 ml of ethanol. 0.32 ml (1.29 mmol) of 4N hydrochloric acid is added, and the mixture is heated at reflux for 2 h. The mixture is made alkaline using concentrated aqueous sodium hydroxide solution, diluted with water and extracted with ethyl acetate. The organic phase is separated off and concentrated. The crude product is purified by preparative HPLC. This gives the title compound as crystals.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated off
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-96da8a147eb0402082ce02d18d729319
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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