Hydrochloric Acid → HCID 178456878, compound

HRID 1821596Notes

Reaction equation

HRID 1821596 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])=[N:14][C:15]=2[NH:17][CH2:18][C@@H:19]([O:21][C:22](=[O:29])[C@@H:23]([NH:27]C)[CH:24]([CH3:26])[CH3:25])[CH3:20])[N:10](OCCC[Si](C)(C)C)[N:9]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])=[N:14][C:15]=2[NH:17][CH2:18][CH:19]([O:21][C:22](=[O:29])[CH:23]([NH2:27])[CH:24]([CH3:26])[CH3:25])[CH3:20])[NH:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86611045HCID 86611045, compound

Product 1

HCID 178456878HCID 178456878, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-3-methyl-2-methylamino-butyric acid (S)-2-[3-(2-chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1-(3-trimethylsilanyl-propoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-1-methyl-ethyl ester (15 mg, 0.0197 mmol), HCl (1 mL of 5N aqueous solution) and dioxane (1 mL) was heated to 80° C. for 30 minutes and then cooled to room temperature. The reaction mixture was made mildly basic by addition of saturated aqueous sodium bicarbonate solution, and the resulting precipitate was filtered, washed with water and dried under vacuum to afford 7 mg of 2-amino-3-methyl-butyric acid 2-[3-(2-chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-1-methyl-ethyl ester.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9b20fc132bfe45ea8bc6af729db19835
Source dataset
uspto-grants-2009_10
Patent number
US07608603B2

Reaction notes

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