Methanol → HCID 178522236、化合物

HRID 629105ノート

反応式

HRID 629105 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178522236HCID 178522236、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ff1e2bda395840289b8276abe913cb32
出典データセット
uspto-grants-2016_04
特許番号
US09315489B2

反応ノート

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