Ammonium Chloride → HCID 86672761、化合物

HRID 1754910ノート

反応式

HRID 1754910 の反応式
[F:1][C:2]([F:16])([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([NH2:32])([C:30]#[N:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][C:27]([C:30]#[N:31])([NH:32][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([O:6][C:2]([F:1])([F:16])[CH:3]([F:4])[F:5])=[CH:15][CH:14]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27766394-(1,1,2,2-Tetrafluoroethoxy)benzoic acidHCID 22091429tert-Butyl 4-amino-4-cyanopiperidine-1-carboxylate

生成物 1

HCID 86672761HCID 86672761、化合物収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uoronium hexafluorophosphate (1.60 g, 4.20 mmol) was added to a solution of 4-(1,1,2,2-tetrafluoro-ethoxy)-benzoic acid (1.00 g, 4.20 mmol), 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (995 mg, 4.42 mmol) and N,N-diisopropylethylamine (1.46 ml, 8.39 mmol) in DMF (8.8 ml) at 0° C. The mixture was gradually warmed to room temperature and stirred for 28.5 hours. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate three times. The organic layers were sequentially washed with H2O (×2) and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (hexane:AcOEt=90:10→30:70) to give 4-cyano-4-[4-(1,1,2,2-tetrafluoro-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester as a light brown powder (1.60 g, 86%).

後処理

  1. extractionfollowed by extraction with ethyl acetate three times
  2. washThe organic layers were sequentially washed with H2O (×2) and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (hexane:AcOEt=90:10→30:70)

出典と根拠

ORDレコード
ord-1201384aa0684e1a9a0869406b570194
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

読み込み中…