Water → HCID 67168993、化合物

HRID 1506467ノート

反応式

HRID 1506467 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3CCOCC3)=[CH:7][CH2:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32]1([C:38]2[C:42]([C:43]([F:46])([F:45])[F:44])=[C:41]([C:47](F)=[O:48])[O:40][N:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.NO.C([O-])(=[O:55])C.[Na+].O>C(#N)C.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH:7]([C:47]([OH:48])([C:41]4[O:40][N:39]=[C:38]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:42]=4[C:43]([F:46])([F:45])[F:44])[O:55][N:19]=3)[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[C:10]=2[CH:11]=1

参加物

9

反応物 6

HCID 962WaterHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58374067HCID 58374067、化合物HCID 67171234HCID 67171234、化合物

生成物 1

HCID 67168993HCID 67168993、化合物収率 6%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a homogeneous solution of tert-butyl 7-bromo-4-morpholinoquinoline-1(2H)-carboxylate (Preparation 77A, 0.598 g, 1.513 mmol) and triethylamine (0.419 mL, 3.03 mmol) in acetonitrile (20 mL) at 0° C. was added a solution of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (I-4, 0.392 g, 1.51 mmol) in acetonitrile (1.0 mL). The reaction mixture was stirred at 0° C. for 2.5 hours and then overnight at room temperature. A homogeneous solution of hydroxylamine hydrochloride (0.421 g, 6.05 mmol) and sodium acetate (0.496 g, 6.05 mmol) in water (0.981 mL, 54.5 mmol) was added, and the reaction mixture was heated at 45° C. for 60 min. The reaction mixture was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under vacuum afforded the crude product which was chromatographed using silica gel chromatography eluting with a 10% mixture of ethyl acetate in hexane to give tert-butyl 7-bromo-3-hydroxy-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3a,4-dihydroisoxazolo[4,3-c]quinoline-5(3H)-carboxylate (0.050 g, 0.086 mmol, 6% yield) as a yellowish solid. The product had LC/MS M+1=636.2 and 637.2.

後処理

  1. customovernight
  2. customat room temperature
  3. temperaturethe reaction mixture was heated at 45° C. for 60 min
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under vacuum
  7. customafforded the crude product which
  8. customwas chromatographed
  9. washeluting with a 10% mixture of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d1fec1cf0a0a46d796ad91533dd01cdc
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

読み込み中…