Hydrochloric Acid → HCID 178515866, compound

HRID 2279166Notes

Reaction equation

HRID 2279166 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[N:18]=[C:17]3[N:28](C4CCCCO4)[N:29]=[C:30]([CH:31]4[CH2:33][CH2:32]4)[C:16]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.Cl>O1CCOCC1>[CH:31]1([C:30]2[C:16]3[C:17](=[N:18][C:19]([C:21]4[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[NH:28][N:29]=2)[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 136623244HCID 136623244, compound

Product 1

HCID 178515866HCID 178515866, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

600 mg of 4-[3-cyclopropyl-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester were dissolved in 6 ml of 1,4-dioxane and 2 ml of dichloromethane and treated with 4.8 ml of hydrochloric acid (4M in dry dioxane). After standing at rt for 16 h the volatiles were removed in vacuo. The residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient) and 315 mg (73%) of the title compound were obtained as hydrochloride.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was purified by preparative HPLC (C18 column, acetonitrile/water gradient)

Sources & evidence

ORD record
ord-66f92e8d1f714dbaba8b0904babdf763
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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