Sulfuric Acid → HCID 9807043、化合物

HRID 1936322ノート

反応式

HRID 1936322 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:35]4[CH:36]=[N:37][C:38]([Cl:41])=[CH:39][CH:40]=4)(N=CC4C=CC(OC)=CC=4)[C:19]4[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=4)[CH:16]=3)[N:11]([CH2:42][CH:43]3[CH2:45][CH2:44]3)[C:10](=[O:46])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:48].N([O-])=O.[Na+].C(OCC)(=O)C>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[C:12](=[CH:17][CH:16]=[C:15]([C:18]([C:35]4[CH:36]=[N:37][C:38]([Cl:41])=[CH:39][CH:40]=4)([OH:48])[C:19]4[N:20]([CH3:24])[CH:21]=[N:22][CH:23]=4)[CH:14]=3)[N:11]([CH2:42][CH:43]3[CH2:45][CH2:44]3)[C:10](=[O:46])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 120507314-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-oneHCID 23668193Sodium Nitrite

生成物 1

HCID 9807043HCID 9807043、化合物収率 94%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of the title compound of Example 43 (4.31 g, 6.64 mmol) in THF (30 ml) was added 38 ml of 1N sulfuric acid. After the mixture was cooled to 0° C., a solution of sodium nitrite (NaNO2, 1.45 g, 20.99 mmol) in water (10 ml) was added dropwise. The reaction mixture was stirred at ambient temperature for 7 hours after which time ethyl acetate was added. The organic layer was washed with saturated potassium carbonate, brine, dried over MgSO4 and concentrated under vacuum to give the crude product. It was chromatographed on silica gel with MeOH-CHCl3—NH4OH (2:98:0.1) as the eluents to afford the title compound of Example 6, 4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-1H-quinolin-2-one as a white solid (3.32 g, 94% yield).

後処理

  1. additionwas added
  2. washThe organic layer was washed with saturated potassium carbonate, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customto give the crude product
  6. customIt was chromatographed on silica gel with MeOH-CHCl3—NH4OH (2:98:0.1) as the eluents

出典と根拠

ORDレコード
ord-a7254eb82a17451bb086790137e1e585
出典データセット
uspto-grants-2002_05
特許番号
US06388092B2

反応ノート

読み込み中…