(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 877066노트

반응식

HRID 877066 반응식
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

참가 물질

4

반응물 1

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

생성물 1

HCID 573785133-{2-[4-(1-Aminocyclobutyl)phenyl]-3-phenylpyrimido[1,2-b]indazol-7-yl}-benzonitrile수율 22.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9b09a39cba104feeaed6b2fe1418e1ce
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987286B2

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