Hydrochloric Acid → TC-S 7001

HRID 2192179Notes

Reaction equation

HRID 2192179 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]([CH3:19])[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>[Cl:21][C:22]1[N:23]=[C:24]([NH2:29])[N:25]=[C:26]([NH:5][C:4]2[CH:3]=[C:2]([F:1])[C:8]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:16][CH:17]=[C:18]([CH3:19])[C:11]=34)=[C:7]([F:20])[CH:6]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 59740981HCID 59740981, compound

Product 1

HCID 11524200TC-S 7001

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

415 mg (1.51 mmol) of 3,5-difluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline and 321 mg (1.96 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 8 ml of water. 1.96 ml of 1N hydrochloric acid are added, and the mixture is heated at reflux overnight. Using 1N aqueous sodium hydroxide solution, the pH is then adjusted to 10, resulting in the precipitation of crystals. The crystals are filtered off with suction and washed with water. The crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 100:5).

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 crude product is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 100:5)

Sources & evidence

ORD record
ord-63a6b94829fb48e986929c6b80431832
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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