Methanol → HCID 178522236, 화합물

HRID 629105노트

반응식

HRID 629105 반응식
[Si](I)(C)(C)C.C[O:7][C:8]1[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=3)=[O:21])[CH:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1.CO>C(Cl)(Cl)Cl>[OH:7][C:8]1[C:13]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:27][CH:28]=3)=[O:21])[CH:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 722035682'-Methoxy-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

생성물 1

HCID 178522236HCID 178522236, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
60 °C

실험 절차

TMSI (100 μL, 0.734 mmol) was added to a solution of 2′-methoxy-N-(4-(trifluoromethoxy)phenyl)-[3,3′-bipyridine]-5-carboxamide (Example 62, 79 mg, 0.203 mmol) in CHCl3 (4 mL) and the RM was stirred at 60° C. overnight. The RM was cooled to RT, poured into MeOH and the solvent was evaporated off under reduced pressure. The residue was treated with aq. 5% NH3 and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the product which was recrystallized from hot EtOAc to afford the title compound as beige crystals. UPLC-MS (Condition 2) tR0.87 min, m/z=376.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 6.38 (t, J=6.65 Hz, 1H) 7.40 (d, J=8.99 Hz, 2H) 7.51 (d, J=6.26 Hz, 1H) 7.86-7.96 (m, 3H) 8.61-8.66 (m, 1H) 9.00-9.04 (m, 1H) 9.09-9.13 (m, 1H) 10.63 (s, 1H) 12.03 (br. s, 1H).

후처리

  1. temperatureThe RM was cooled to RT
  2. customthe solvent was evaporated off under reduced pressure
  3. additionThe residue was treated with aq. 5% NH3
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give the product which
  9. customwas recrystallized from hot EtOAc

출처 및 근거

ORD 기록
ord-ff1e2bda395840289b8276abe913cb32
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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