Hydrochloric Acid → N4-(3-Fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}phenyl)-6-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 2192191Notes

Reaction equation

HRID 2192191 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[C:18]([CH2:19][CH2:20][O:21][CH3:22])[C:11]=12)[NH2:5].Cl[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:27]=[C:26]([NH2:34])[N:25]=1.Cl.N1C=CC=CC=1N.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[N:27]=[C:26]([NH2:34])[N:25]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[C:18]([CH2:19][CH2:20][O:21][CH3:22])[C:11]=12

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 104392-AminopyridineHCID 14798Sodium HydroxideHCID 130869074-Chloro-6-(trifluoromethyl)pyrimidin-2-amineHCID 597410123-Fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}aniline

Product 1

HCID 11547139N4-(3-Fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}phenyl)-6-(trifluoromethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

53 mg (0.18 mmol) of 3-fluoro-4-{[3-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}aniline and 42 mg (0.21 mmol) of 4-chloro-6-(trifluoromethyl)pyrimidine-2-amine are suspended in 4 ml of water. 0.23 ml (0.23 mmol) of 1N hydrochloric acid is added, and the mixture is heated at reflux overnight. Another 22 mg (0.11 mmol) of 4-chloro-6-trifluoromethyl)pyridine-2-amine are then added, and the mixture is again heated overnight. By addition of 1N aqueous sodium hydroxide solution, the pH is adjusted to 10, resulting in the precipitation of crystals. The crystals are filtered off with suction and washed with water. The product is purified by preparative HPLC.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the precipitation of crystals
  4. filtrationThe crystals are filtered off with suction
  5. washwashed with water
  6. customThe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-c0197804f99943078c389157244e86e4
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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