Sulfuric Acid → 1-(2-(3-(4-Methoxyhepta-1,6-dien-4-yl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea

HRID 132610

反応式

HRID 132610 の反応式
[OH:1][C:2]([C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][CH:36]=1)[O:12][C:13]1[C:18]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH2:6][CH:7]=[CH2:8])[CH2:3][CH:4]=[CH2:5].S(=O)(=O)(O)O.[C:42](=O)(O)[O-].[Na+]>CO>[CH3:42][O:1][C:2]([C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][CH:36]=1)[O:12][C:13]1[C:18]([NH:19][C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]([F:33])([F:31])[F:32])=[CH:27][CH:28]=2)=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=1)([CH2:6][CH:7]=[CH2:8])[CH2:3][CH:4]=[CH2:5]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 685297861-(2-(3-(4-Hydroxyhepta-1,6-dien-4-yl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea

生成物 1

HCID 685315581-(2-(3-(4-Methoxyhepta-1,6-dien-4-yl)phenoxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of Example 640 (120 mg, 0.24 mmol) in dry methanol (15 mL) was added concentrated sulfuric acid (2 mL) at rt. The mixture was heated to 100° C. for 72 h and cooled down to rt. A saturated solution of sodium bicarbonate was slowly added and the mixture was extracted with dichloromethane. Evaporation afforded a residue which was purified by reverse phase preparative HPLC. (M+H)+=514. 1H NMR (400 MHz, DMSO-d6) δppm 2.62 (m, 4 H), 3.08 (s, 3H), 5.03 (m, 4H), 5.55 (m, 2H), 7.31 (m, 7H), 7.57 (d, 2H, J=9.1 Hz), 7.70 (dd, J=5.0, 1.7 Hz, 1H), 8.55 (dd, J=7.8, 1.5 Hz, 1H), 8.72 (s, 1H), 9.56 (s, 1H).

後処理

  1. temperaturecooled down to rt
  2. extractionthe mixture was extracted with dichloromethane
  3. customEvaporation
  4. customafforded a residue which
  5. customwas purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-f05fabe6251a493db7197d000491b851
出典データセット
uspto-grants-2008_06
特許番号
US07388021B2

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