4-Hydroxybenzaldehyde → HCID 178486396, 화합물

HRID 253218노트

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HRID 253218 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:14](=O)[CH:15]([CH3:17])[CH3:16])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:19][NH2:20].[OH:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>C(O)C>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[CH3:16][CH:15]([C:14]1[C:11]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][C:6]=3[C:26]([C:25]3[CH:28]=[CH:29][C:22]([OH:21])=[CH:23][CH:24]=3)=[N:13][C:12]=2[NH:20][N:19]=1)[CH3:17]

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 43157030HCID 43157030, 화합물

생성물 1

HCID 178486396HCID 178486396, 화합물수율 33%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

2-[3,4-bis(methyloxy)phenyl]-4-methyl-3-oxopentanenitrile (100 mg, 0.40 mmol) was dissolved in ethanol (1 mL), and anhydrous hydrazine (98%, 16 μL, 0.52 mmol) was added. The resulting mixture was heated at reflux for 1 hour. It was cooled, concentrated, and the residue was dried in vacuum for one hour. To this residue was added of 4-hydroxybenzaldehyde (74 mg, 0.61 mmol) and trifluoroacetic acid (1 mL), and the mixture was heated at 70° C. for 18 hours. Then the reaction mixture was concentrated, dissolved in 10 mL of N,N-dimethylformamide and purified by preparatory HPLC (Shimadzu LC-8A HPLC, Waters Xterra C18 30 mm×100 mm column, acetonitrile-water-trifluoroacetic eluent). After concentration and lyophillization of the pure fractions 4-[1-(1-methylethyl)-7,8-bis(methyloxy)-3H-pyrazolo[3,4-c]isoquinolin-5-yl]phenol trifluoroacetic acid salt (60 mg, 0.13 mmol, 33% yield) was obtained. 1H NMR (400 MHz, d6-DMSO): 7.62-7.60 (d, 2H), 7.58 (s, 1H), 7.55 (s, 1H), 6.98-6.96 (d, 2H), 4.04 (s, 3H), 3.77-3.75 (m, 1H), 3.76 (s, 3H), 1.49-1.46 (d, 2H); MS (EI) for C21H21N3O3: 363 (MH+).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureIt was cooled
  4. concentrationconcentrated
  5. customthe residue was dried in vacuum for one hour
  6. concentrationThen the reaction mixture was concentrated
  7. dissolutiondissolved in 10 mL of N,N-dimethylformamide
  8. custompurified by preparatory HPLC (Shimadzu LC-8A HPLC, Waters Xterra C18 30 mm×100 mm column, acetonitrile-water-trifluoroacetic eluent)

출처 및 근거

ORD 기록
ord-e12cf4c2798e4134b75f78cf9c6002cf
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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