D-Camphorsulfonic Acid → HCID 69812522, 화합물

HRID 888448

반응식

HRID 888448 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 69812522HCID 69812522, 화합물수율 79%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7578d5d25cc34485b5cdb7958ec3a929
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247550B2

연결된 노트

불러오는 중…