1-Hydroxybenzotriazole → HCID 71510275、化合物

HRID 83492ノート

反応式

HRID 83492 の反応式
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:10][C:9]([NH2:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][C@H:25]1[C:29](=[O:30])[NH:28][CH2:27][C@@H:26]1[C:31](O)=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=3)=[CH:10][C:9]([NH:23][C:31]([C@@H:26]3[C@@H:25]([CH3:24])[C:29](=[O:30])[NH:28][CH2:27]3)=[O:32])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712877301-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamineHCID 86680348(3R,4R)-4-Methyl-5-oxopyrrolidine-3-carboxylic Acid

生成物 1

HCID 71510275HCID 71510275、化合物収率 57.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine (79 mg) in N,N-dimethylformamide (0.8 ml) were sequentially added (3R,4R)-4-methyl-5-oxopyrrolidine-3-carboxylic acid (46 mg) prepared in Preparation 1, HOBt.H2O (57 mg) and WSC.HCl (71 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added water and a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (63 mg).

後処理

  1. extractiona saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-059f61f92b154ebd94a1d7041508eeb3
出典データセット
uspto-grants-2014_09
特許番号
US08846746B2

反応ノート

読み込み中…