Sulfuric Acid → HCID 44546064、化合物

HRID 1958657ノート

反応式

HRID 1958657 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[N:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]#[N:5].[OH:33]S(O)(=O)=O.[NH4+].[OH-]>C(O)(=O)C.O>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[N:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]([NH2:5])=[O:33]

参加物

6

反応物 3

HCID 1118Sulfuric Acid2 回HCID 14923Ammonium HydroxideHCID 44545869HCID 44545869、化合物

生成物 1

HCID 44546064HCID 44546064、化合物収率 68%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 78, prepared according to the method described in US 2008/0319012 A1) (130 mg, 0.31 mmol) in acetic acid (3 mL) was added conc. H2SO4 (0.7 mL) and the mixture was stirred at 100° C. After 2 hours, more conc. H2SO4 (0.2 mL) was added and the mixture was stirred at 100° C. for 1 hour. Then the reaction mixture was cooled to room temperature, diluted with H2O (10 mL) in the ice bath, and neutralized by addition of NH4OH solution to pH 7. The mixture was extracted with CH2Cl2 (3 times) and then the organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:10 (v/v)) to afford the solid, which was recrystallized from CH2Cl2/MeOH/Et2O to give the title compound (131.6 mg, 68%). 1H NMR (300 MHz, CD3OD) δ 2.53 (3H, s), 4.23 (2H, s), 7.16-7.23 (3H, m), 7.54-7.59 (2H, m), 7.84 (1H, dd), 8.04 (2H, bs), 8.25 (1H, bs), 8.85 (2H, dd). MS (ESI) m/z 439 (MH+).

後処理

  1. stirringthe mixture was stirred at 100° C. for 1 hour
  2. temperatureThen the reaction mixture was cooled to room temperature
  3. extractionThe mixture was extracted with CH2Cl2 (3 times)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:10 (v/v))
  8. customto afford the solid, which
  9. customwas recrystallized from CH2Cl2/MeOH/Et2O

出典と根拠

ORDレコード
ord-54a0e568744e49fbb8d04beb19dfccc0
出典データセット
uspto-grants-2013_04
特許番号
US08410146B2

反応ノート

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