Thiobenzamide → 2-Phenyl-4-(2-phenylpyrimidin-5-yl)thiazole

HRID 42306

反応式

HRID 42306 の反応式
Br[CH2:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][CH:10]=1)=O.[C:17]([NH2:25])(=[S:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([C:17]2[S:24][CH:2]=[C:3]([C:5]3[CH:6]=[N:7][C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][CH:10]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 683563ThiobenzamideHCID 592524542-Bromo-1-(2-phenylpyrimidin-5-yl)ethanone

生成物 1

HCID 592524472-Phenyl-4-(2-phenylpyrimidin-5-yl)thiazole収率 46%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture consisting of 2-bromo-1-(2-phenylpyrimidin-5-yl)ethanone (Example 14, Step B, 50 mg, 0.18 mmol), thiobenzamide (TCl America, 25 mg, 0.18 mmol) and absolute ethanol (4 mL) in a capped scintillation vial was heated to near boiling for several minutes and was subsequently allowed to cool to room temperature. A white solid precipitated within minutes. The precipitate was collected by vacuum filtration. Light ethanol rinse, suction, and drying under high vacuum at room temperature afforded the title compound (26 mg, 46% yield) as an off-white solid; melting point 214.4-216.1° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.54 (s, 2H), 8.54 (s, 1H), 8.47 (m, 2H), 8.08 (m, 2H), 7.62-7.54 (m, 6H); LC/MS (ESI+) m/z 316.1, (ESI−) m/z 337.2 (M−1+Na+); H-PGDS FPBA IC50: >20 μM.

後処理

  1. temperaturewas heated
  2. waitto near boiling for several minutes
  3. customA white solid precipitated within minutes
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washLight ethanol rinse
  6. customsuction, and drying under high vacuum at room temperature

出典と根拠

ORDレコード
ord-59b63460ac33409aa614d4fadb29ae68
出典データセット
uspto-grants-2013_09
特許番号
US08536185B2

関連ノート

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