D-Camphorsulfonic Acid → HCID 69812522、化合物

HRID 888448

反応式

HRID 888448 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([CH2:14][CH3:15])[CH2:12][CH2:11][NH:10][C:9]2=[O:16])=[CH:4][CH:3]=1.Br[C:18]1[C:19](=[O:26])[N:20]([CH3:25])[CH:21]=[C:22]([Br:24])[N:23]=1.[CH3:27]C1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O>C(O)(C)C>[Br:24][C:22]1[N:23]=[C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[C:9](=[O:16])[NH:10][CH2:11][CH2:12][N:13]3[CH2:14][CH3:15])=[CH:6][CH:7]=2)[C:19](=[O:26])[N:20]([CH2:25][CH3:27])[CH:21]=1

参加物

5

反応物 3

HCID 65617D-Camphorsulfonic AcidHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 576251673-(4-Aminophenyl)-4-ethylpiperazin-2-one

生成物 1

HCID 69812522HCID 69812522、化合物収率 79%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 33 (450 mg, 2.05 mmol), isopropanol (5 mL), 13 (603 mg, 2.26 mmol) and DL-10-camphorsulfonic acid (813 mg, 3.50 mmol), and the reaction mixture was then stirred at reflux for 16 h. After this time, the reaction mixture was cooled to room temperature, filtered and the filter cake washed with isopropanol (10 mL). The resulting solid was dissolved in methylene chloride/methanol (3:1), absorbed onto silica gel and purified by flash chromatography to afford 34 in 79% yield (654 mg) as an orange solid: mp 152-153° C.; 1H NMR (500 MHz, CDCl3) 8.28 (bs, 1H 7.73 (d, 2H, J=8.5 Hz), 7.43 (d, 2H, J=8.5 Hz), 6.74 (s, 1H), 5.90 (d, 1H, J=3.5 Hz), 4.12 (s, 1H), 3.60 (m, 1H), 3.52 (s, 3H), 3.36 (m, 1H), 3.12 (m, 1H), 2.60 (m, 2H), 2.28 (m, 1H), 1.00 (t, 3H, J=7.0 Hz); MS (ESI+) m/z 406.0 (M+H).

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureat reflux for 16 h
  4. filtrationfiltered
  5. washthe filter cake washed with isopropanol (10 mL)
  6. dissolutionThe resulting solid was dissolved in methylene chloride/methanol (3:1)
  7. customabsorbed onto silica gel
  8. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-7578d5d25cc34485b5cdb7958ec3a929
出典データセット
uspto-grants-2012_08
特許番号
US08247550B2

関連ノート

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