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

HRID 42306

반응식

HRID 42306 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59b63460ac33409aa614d4fadb29ae68
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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