(1-{4-[9-(3-Cyanophenyl)-3-phenylpyrimido[1,2-b]indazol-2-yl]phenyl}-cyclobutyl)carbamic acid tert-butyl ester → 3-{2-[4-(1-Aminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazol-9-yl}-benzonitrile

HRID 877062Notes

Reaction equation

HRID 877062 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]=[C:26]([C:29]6[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=6)[CH:25]=[CH:24]5)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C>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]=[C:26]([C:29]6[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=6)[C:35]#[N:36])[CH:25]=[CH:24]5)=[C:20]4[N:19]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 86702536(1-{4-[9-(3-Cyanophenyl)-3-phenylpyrimido[1,2-b]indazol-2-yl]phenyl}-cyclobutyl)carbamic acid tert-butyl ester

Product 1

HCID 573782023-{2-[4-(1-Aminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazol-9-yl}-benzonitrileYield 40.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

126.9 mg (0.21 mmol) (1-{4-[9-(3-Cyanophenyl)-3-phenylpyrimido[1,2-b]indazol-2-yl]phenyl}cyclobutyl)carbamic acid tert-butyl ester in 7 mL 4M hydrogen chloride in dioxane were stirred over night at room temperature. The solvent was evaporated and the residue was treated with saturated sodium bicarbonate solution. After extraction with dichloromethane (three times) the combined organic extracts were washed with brine, dried (sodium sulfate) and filtrated. The solvent was removed and the residue (102 mg) was purified by HPLC yielding 42 mg (37.9%) of the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with saturated sodium bicarbonate solution
  3. extractionAfter extraction with dichloromethane (three times) the combined organic extracts
  4. washwere washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltrated
  7. customThe solvent was removed
  8. customthe residue (102 mg) was purified by HPLC

Sources & evidence

ORD record
ord-2d443e20f5d240508433b58721eb5eee
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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