Sulfuric Acid → HCID 9807043, 화합물

HRID 1936322노트

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HRID 1936322 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 9807043HCID 9807043, 화합물수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7254eb82a17451bb086790137e1e585
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06388092B2

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