HCID 67973853, compound → HCID 57377871, compound

HRID 877059Notes

Reaction equation

HRID 877059 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:37][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][C:25]([C:29]6[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=6)=[CH:24]5)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(C1C=C(C2C(C3C=CC=CC=3)=CN3N=C4C(C=CC(C5C=C(C=CC=5)C#N)=C4)=C3N=2)C=CC=1)#N>Cl.O1CCOCC1>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:37][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][C:25]([C:29]6[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=6)[C:35]#[N:36])=[CH:24]5)=[C:20]4[N:19]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 67973853HCID 67973853, compoundHCID 86702534HCID 86702534, compound

Product 1

HCID 57377871HCID 57377871, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

239.4 mg (1-{4-[8-(3-Cyanophenyl)-3-phenylpyrimido[1,2-b]indazol-2-yl]phenyl}-cyclobutyl)carbamic acid tert-butyl ester jointly with the byproduct 3-[2-(3-cyanophenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]benzonitrile were dissolved in 17 mL 4M hydrogen chloride in dioxane. After stirring over night at room temperature the solvent was evaporated to dryness and the residue was treated with saturated sodium bicarbonate solution. This aqueous solution was extracted three times with ethyl acetate. The combined organic extracts were worked up as already described. The residue was purified by column chromatography on silicagel (eluents: dichloromethane/methanol) and additional HPLC yielding 18.2 mg of the title compound.

Workup

  1. customwas evaporated to dryness
  2. additionthe residue was treated with saturated sodium bicarbonate solution
  3. extractionThis aqueous solution was extracted three times with ethyl acetate
  4. customThe residue was purified by column chromatography on silicagel (eluents: dichloromethane/methanol) and additional HPLC

Sources & evidence

ORD record
ord-9de1f9ea613e416badf1ac4a6b86b6d7
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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