Trifluoroacetic acid → N-(5-(4-amino-3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-5-iodonicotinamide

HRID 1958187ノート

反応式

HRID 1958187 の反応式
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[N:19][CH:20]=[C:21]([NH:23][C:24]([C:26]3[CH:27]=[N:28][CH:29]=[C:30]([I:32])[CH:31]=3)=[O:25])[CH:22]=2)=[CH:13][C:12]=1[Cl:39])C1C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[C:21]([NH:23][C:24](=[O:25])[C:26]3[CH:31]=[C:30]([I:32])[CH:29]=[N:28][CH:27]=3)[CH:20]=[N:19][C:18]=2[O:33][CH2:34][C:35]([F:36])([F:37])[F:38])=[CH:13][C:12]=1[Cl:39]

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 67282185{2-Chloro-4-[5-[(5-iodo-pyridine-3-carbonyl)-amino]-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-phenyl}-carbamic acid benzyl ester

生成物 1

HCID 56961948N-(5-(4-amino-3-chlorophenyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)-5-iodonicotinamide収率 84.7%

実験手順

{2-Chloro-4-[5-[(5-iodo-pyridine-3-carbonyl)-amino]-2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-phenyl}-carbamic acid benzyl ester (87 mg, 127 μmol) was, with cooling, combined with trifluoroacetic acid (3 mL) to give a brown solution. The reaction mixture was warmed to room temperature and stirred for 72 h. The crude reaction mixture was concentrated in vacuo, poured into 50 mL ethyl acetate and extracted with 1 M NaOH (1×25 mL). The aqueous layer was washed with ethyl acetate (1×50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 0% to 40% EtOAc in heptane) to give the title compound (59 mg, 84%); LC-MS (UV peak area/ESI) 98.1%, 548.9795 (M+H)+.

後処理

  1. temperaturewith cooling
  2. customto give a brown solution
  3. customThe crude reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionpoured into 50 mL ethyl acetate
  6. extractionextracted with 1 M NaOH (1×25 mL)
  7. washThe aqueous layer was washed with ethyl acetate (1×50 mL)
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography (silica gel, 20 g, 0% to 40% EtOAc in heptane)

出典と根拠

ORDレコード
ord-b9e086049e414fe79604febcc9e3a881
出典データセット
uspto-grants-2013_04
特許番号
US08410107B2

反応ノート

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