Hydrochloric Acid → N-[2-Amino-6-(4-pyridinyl)-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-4-yloxy)phenyl]amine

HRID 16442Notes

Reaction equation

HRID 16442 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2)[NH2:5].Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:32])[N:21]=1.Cl.[OH-].[Na+]>O>[NH2:32][C:22]1[N:21]=[C:20]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][C:10]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:11]=3[CH:12]=[N:13][NH:14]4)=[C:2]([F:1])[CH:3]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 179793393-Fluoro-4-(1H-indazol-4-yloxy)anilineHCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 17979321N-[2-Amino-6-(4-pyridinyl)-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-4-yloxy)phenyl]amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 mg (0.19 mmol) of 3-fluoro-4-(1H-indazol-4-yloxy)aniline (from example XXVI) and 40.1 mg (0.19 mmol) of 4-chloro-6-(4-pyridinyl)-2-pyrimidineamine (from example XXIX) are suspended in 2 ml of water, and 27 μl of concentrated hydrochloric acid are added. The reaction mixture is heated at reflux overnight, resulting in the formation of a brown precipitate. Using 1N sodium hydroxide solution, the suspension is adjusted to pH 10. The precipitate is filtered off from the aqueous phase, and the filtrate is discarded. The crude product is purified by HPLC.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the formation of a brown precipitate
  4. filtrationThe precipitate is filtered off from the aqueous phase
  5. customThe crude product is purified by HPLC

Sources & evidence

ORD record
ord-5dc6926c1ddd4da8b216c5ac71a1cc61
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…