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Trifluoroacetic acid → 3-(5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide

HRID 522899
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HRID 522899 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[C:5]([F:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([NH:27][CH3:28])=[O:26].FC(F)(F)C(O)=O>CC(O)C>[F:20][C:5]1[C:6]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)=[N:7][C:2]([NH:21][C:22]2[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=2)[C:25]([NH:27][CH3:28])=[O:26])=[N:3][CH:4]=1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 6765263-Amino-N-methylbenzamideHCID 866852522-Chloro-5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine

생성물 1

HCID 673551243-(5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide수율 100.4%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
84 °C

실험 절차

To 2-chloro-5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine (90.0 mg, 0.302 mmol) and 3-amino-N-methylbenzamide (49.9 mg, 0.333 mmol) in a disposable sealed tube in 2-propanol (2.50 mL) was added trifluoroacetic acid (0.070 mL, 0.907 mmol). The resulting reaction mixture was heated at 84° C. for 3 d, cooled to RT and concentrated. The residue was stirred in EtOAc and saturated aqueous NaHCO3 for 10 min and transferred to a reparatory funnel. The organic layer was washed with brine, dried and concentrated giving 3-(5-fluoro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide (124.8 mg).

후처리

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. concentrationconcentrated
  4. customtransferred to a reparatory funnel
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bca01413f6cb41c1ba481685244a3a3b
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334269B2

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