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Trifluoroacetic acid → 1-[1-(3-Azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1499782
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HRID 1499782 반응식
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]2[N:15]([CH:19]([C:21]3[C:22]([O:40][CH3:41])=[C:23]([CH:29]4[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30]4)[C:24]([CH3:28])=[C:25]([Cl:27])[CH:26]=3)[CH3:20])[N:16]=[C:17]([Br:18])[C:10]=12>C(Cl)Cl.[OH-].[Na+]>[NH:31]1[CH2:32][CH:29]([C:23]2[C:22]([O:40][CH3:41])=[C:21]([CH:19]([N:15]3[C:11]4=[N:12][CH:13]=[N:14][C:9]([NH2:8])=[C:10]4[C:17]([Br:18])=[N:16]3)[CH3:20])[CH:26]=[C:25]([Cl:27])[C:24]=2[CH3:28])[CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 86677708tert-Butyl 3-{3-[1-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate

생성물 1

HCID 866777091-[1-(3-Azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회
HCID 14798
Sodium Hydroxide
용매

실험 절차

Trifluoroacetic acid (1.2 mL, 16 mmol) was added to a solution of tert-butyl 3-{3-[1-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidine-1-carboxylate (224 mg, 0.407 mmol) in methylene chloride (2.5 mL) and stirred for 2 h at room temp. The mixture was diluted with dichloromethane and 1 N NaOH was added and stirred rapidly for a few minutes. The layers were separated and the aqueous extracted with dichloromethane. The combined organics were dried (MgSO4), filtered, and concentrated. Drying in vacuo gave 163 mg (91%) of the freebase. LCMS calculated for C18H21BrClN6O (M+H)+: m/z=451.1; Found: 451.0.

후처리

  1. additionwas added
  2. stirringstirred rapidly for a few minutes
  3. customThe layers were separated
  4. extractionthe aqueous extracted with dichloromethane
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customDrying in vacuo
  9. customgave 163 mg (91%) of the freebase

출처 및 근거

ORD 기록
ord-9a8362cbfe9347f9b1b08adbb0236951
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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