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Hydrochloric Acid → 1207830-66-7

HRID 655718
Notes
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Reaction equation

HRID 655718 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[N:11]1[C:15]2=[N:16][CH:17]=[N:18][C:19]([O:20][C@@H:21]([CH2:32][O:33][C@H:34]([CH3:47])[CH2:35][O:36][Si](C(C)C)(C(C)C)C(C)C)[C:22]([NH:24][C:25]3[CH:30]=[N:29][C:28]([CH3:31])=[CH:27][N:26]=3)=[O:23])=[C:14]2[CH:13]=[N:12]1.C(=O)(O)[O-].[Na+]>CC(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([O:20][C@@H:21]([CH2:32][O:33][C@H:34]([CH3:47])[CH2:35][OH:36])[C:22]([NH:24][C:25]3[CH:30]=[N:29][C:28]([CH3:31])=[CH:27][N:26]=3)=[O:23])[C:14]=2[CH:13]=[N:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 46938169(2S)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyrazin-2-yl)-3-((R)-1-(triisopropylsilyloxy)propan-2-yloxy)propanamide

Product 1

HCID 461756111207830-66-7Yield 84%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Procedure

Hydrochloric acid (6M, 4 equivs) was added with stirring to a solution of (2S)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyrazin-2-yl)-3-((R)-1-(triisopropylsilyloxy)propan-2-yloxy)propanamide (Intermediate AZ1) (1 equiv) in propan-2-ol (9 rel vols) in an inert atmosphere at ambient temperature. The mixture was stirred for 6 hours then basified carefully with aqueous sodium bicarbonate solution. The volume was reduced to half of the original volume by distillation under reduced pressure and then ethyl acetate and water were added. The mixture was stirred and then the phases were separated. The aqueous phase was extracted with ethyl acetate and the combined organic extract and washings were dried by azeotropic distillation. The product was crystallised from a mixture of ethyl acetate/heptane (5:6 vols). Yield 84%.

Workup

  1. distillationThe volume was reduced to half of the original volume by distillation under reduced pressure
  2. additionethyl acetate and water were added
  3. stirringThe mixture was stirred
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. extractionthe combined organic extract
  7. customwashings were dried by azeotropic distillation
  8. customThe product was crystallised from a mixture of ethyl acetate/heptane (5:6 vols)

Sources & evidence

ORD record
ord-38a18938f2154739a2c9e597a73b66e3
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071608B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes