Hydrochloric Acid → HCID 178483197, compound

HRID 82032Notes

Reaction equation

HRID 82032 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:31](/[CH:32]=[CH:33]/[C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][N:41]([CH3:43])[CH3:42])[CH:35]=4)=[N:30][N:29](C4CCCCO4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH:21]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO>[CH3:42][N:41]([CH2:40][C:36]1[CH:35]=[C:34](/[CH:33]=[CH:32]/[C:31]2[C:17]3[C:18](=[N:19][C:20]([C:22]4[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=4)=[CH:21][C:16]=3[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:15])[NH:29][N:30]=2)[CH:39]=[CH:38][CH:37]=1)[CH3:43]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 136359498HCID 136359498, compound

Product 1

HCID 178483197HCID 178483197, compoundYield 117.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold solution (0° C.) of 4-[3-[(E)-2-(3-dimethylaminomethyl-phenyl)-vinyl]-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.25 g, 0.37 mmol) in dry methanol (5 ml) was added dropwise a solution of aqueous 6N HCl (0.7 ml, 3.8 mmol). The reaction mixture was allowed to warm to room temperature and stirring was pursued for 2 hours before being concentrated under reduced pressure. Aqueous 6N HCl (0.7 ml, 3.8 mmol) was added to the crude mixture and stirring was pursued for another hour. Solvents were evaporated under vacuum, methanol and diethyl ether were added, the resulting precipitate was filtered and dried to give a chlorhydrate salt of the title compound as an orange solid (0.21 g; 95%).

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. stirringstirring
  3. waitwas pursued for another hour
  4. customSolvents were evaporated under vacuum, methanol and diethyl ether
  5. additionwere added
  6. filtrationthe resulting precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-82ab6fe3b439422da71868bac44dd959
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

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