(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-7-yl}-benzonitrile

HRID 877066Notes

Reaction equation

HRID 877066 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:27]5[C:28]([CH:23]=[CH:24][CH:25]=[C:26]5[C:29]5[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=5)[C:35]#[N:36])=[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 573785133-{2-[4-(1-Aminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazol-7-yl}-benzonitrileYield 22.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

172 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 12 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 crude residue (117 mg) was purified by HPLC yielding 23 mg 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 crude residue (117 mg) was purified by HPLC

Sources & evidence

ORD record
ord-9b09a39cba104feeaed6b2fe1418e1ce
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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