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

HRID 522895
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HRID 522895 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)[CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26][CH3:27])=[O:25].FC(F)(F)C(O)=O>CC(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([NH:26][CH3:27])=[O:25])[N:7]=3)[CH2:9]2)=[CH:14][CH:15]=1
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 6765263-Amino-N-methylbenzamideHCID 866852492-Chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine

생성물 1

HCID 533735373-(4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide수율 97.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
84 °C

실험 절차

To 2-chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidine (90.0 mg, 0.322 mmol) and 3-amino-N-methylbenzamide (53.2 mg, 0.354 mmol) in a disposable sealed tube in 2-propanol (2.50 mL) was added trifluoroacetic acid (0.074 mL, 0.965 mmol). The resulting reaction mixture was heated at 84° C. for 18 h, cooled to RT, concentrated, taken up in MeOH-DCM, filtered through an SCX-2 column with MeOH. The product was eluted with 2.0 M NH3 in MeOH. Fractions containing the product were concentrated to afford 3-(4-(3-(4-fluorophenoxy)azetidin-1-yl)pyrimidin-2-ylamino)-N-methylbenzamide (123.9 mg).

후처리

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. concentrationconcentrated
  4. filtrationfiltered through an SCX-2 column with MeOH
  5. washThe product was eluted with 2.0 M NH3 in MeOH
  6. additionFractions containing the product
  7. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-ace9539fe0344949abb5514f15d1a121
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334269B2

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