3-Acetylpyridine → HCID 178523513、化合物

HRID 1093745ノート

反応式

HRID 1093745 の反応式
CCN(C(C)C)C(C)C.Cl.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[NH:21][N:20]=[C:19]([C:22]([OH:24])=O)[CH:18]=2)[CH:12]=1.C(C1C=NC=CC=1)(=O)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:57][CH2:58][C:59]([N:61]1[CH2:66][CH2:65][CH:64]([O:67][C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([C:74]([F:77])([F:76])[F:75])[CH:69]=2)[CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.O>[O:60]=[C:59]([N:61]1[CH2:62][CH2:63][CH:64]([O:67][C:68]2[CH:73]=[CH:72][CH:71]=[C:70]([C:74]([F:77])([F:75])[F:76])[CH:69]=2)[CH2:65][CH2:66]1)[CH2:58][NH:57][C:22]([C:19]1[CH:18]=[C:17]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[NH:21][N:20]=1)=[O:24]

参加物

9

反応物 6

HCID 95893-AcetylpyridineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665915472-Amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochlorideHCID 1784797413-(3-Pyridinyl)-1H-pyrazole-5-carboxylic acid hydrochloride

生成物 1

HCID 178523513HCID 178523513、化合物収率 66%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (290 mg, 2.26 mmol) was added to a stirred solution of 5-pyridin-3-yl-1H-pyrazole-3-carboxylic acid hydrochloride (prepared by the method used for the synthesis of Intermediate 29, starting from 3-acetylpyridine) (100 mg, 0.44 mmol) in DMF (2 mL) followed by HOBt (63 mg, 0.46 mmol) and EDCI.HCl (90 mg, 0.46 mmol). After 5 minutes 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (150 mg, 0.44 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by filtering through 60-120 silica gel column and filtrate collected was concentrated under reduced pressure to afford 138 mg (66% Yield) of 5-pyridin-3-yl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 474, 94.7%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (s, 1H), 9.4 (s, 1H), 8.56 (d, 1H), 8.16 (m, 1H), 7.46 (m, 2H), 7.22 (m, 4H), 4.8 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.44 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

後処理

  1. customprepared by the method
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure The residue
  6. customwas purified
  7. filtrationby filtering through 60-120 silica gel column and filtrate
  8. customcollected
  9. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-e098ea6551c749ab85bbdea66b984d6e
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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