Hydrochloric Acid → HCID 118208676, compound

HRID 595269Notes

Reaction equation

HRID 595269 reaction equation
Cl.[F:2][CH:3]([F:31])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][CH:24]4[CH2:28][O:27]C(C)(C)[O:25]4)[CH:22]=3)[CH:12]=2)[N:5]=1.O.[OH-].[Na+]>CO>[F:31][CH:3]([F:2])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]2[CH:12]=[C:13]([C:18]3[CH:19]=[N:20][N:21]([CH2:23][CH:24]([OH:25])[CH2:28][OH:27])[CH:22]=3)[CH:14]=[C:15]([CH3:17])[CH:16]=2)[N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118208849HCID 118208849, compound

Product 1

HCID 118208676HCID 118208676, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrochloric acid (6N, 6.6 mL, 39.7 mmol) was added to 4-(difluoromethyl)-N-(3-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-4-yl)-5-methylphenyl)pyrimidin-2-amine (16.5 g, 39.7 mmol) in MeOH (150 mL). The mixture heated at reflux for 2 h then cooled to RT. Water (200 mL) was added and then the pH was adjusted to 7 with NaOH (6N). The solution was seeded with crystalline product (prepared via an earlier small scale) and crystallization occurred. Additional water (150 ml) was added and the mixture was stirred for 30 min, then filtered, washed with water (2×50 mL) and dried for 14 h under a nitrogen bag to afford 3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propane-1,2-diol an off white solid.

Workup

  1. temperatureThe mixture heated
  2. temperatureat reflux for 2 h
  3. customprepared via an earlier small scale) and
  4. customcrystallization
  5. additionAdditional water (150 ml) was added
  6. filtrationfiltered
  7. washwashed with water (2×50 mL)
  8. customdried for 14 h under a nitrogen bag

Sources & evidence

ORD record
ord-843b628804d6433a84211a5cae1ff852
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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