1,2-Dichloroethane → (R)-2-(4-bromophenoxy)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acetamide

HRID 511857

反応式

HRID 511857 の反応式
Cl.Cl.[F:3][C:4]([F:17])([F:16])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]([NH2:15])[CH3:14])=[N:11][CH:12]=1.[Br:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][C:25](O)=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.N>ClCCl>[Br:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][C:25]([NH:15][C@@H:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([F:3])([F:16])[F:17])=[CH:12][N:11]=2)[CH3:14])=[O:26])=[CH:21][CH:20]=1

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 74657p-Bromophenoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 12820921Azane;hydrochlorideHCID 66892447(1R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethan-1-amine dihydrochloride

生成物 1

HCID 49792855(R)-2-(4-bromophenoxy)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acetamide収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethanamine 2HCl salt (173 mg, 0.79 mmol) and 2-(4-bromophenoxy)acetic acid (200 mg, 0.87 mmol) in dichloromethane (5 mL) were added triethylamine (400 mg, 3.9 mmol), EDC (180 mg, 0.94 mmol) and HOBT (60 mg, 0.39 mmol) respectively. The reaction mixture was stirred at room temperature for 18 hours. Sat. ammonia hydrochloride aqueous solution was added to the mixture. The organic layer was extracted with ethyl acetate, washed with brine, and dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a hexane/ethylacetate=2/1 (v/v) to furnish 276 mg (81% yield) of the title as a colorless oil;

後処理

  1. extractionThe organic layer was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter the filtration
  5. customto separate solvent and sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customto give the residue, which
  8. washeluted with a hexane/ethylacetate=2/1 (v/v)
  9. customto furnish 276 mg (81% yield) of the title as a colorless oil

出典と根拠

ORDレコード
ord-0c0ebec6a11c481393fb389952510e81
出典データセット
uspto-grants-2015_08
特許番号
US09101616B2

関連ノート

読み込み中…