Methane → HCID 178508343, 화합물

HRID 646735노트

반응식

HRID 646735 반응식
[NH2:1][C:2]1[C:3]([C:16]#[N:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][N:7]=1.[C:18]([NH:26][NH2:27])(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C=O)C.C>CCOC(C)=O.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:16]1[NH:17][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][N:27]=1

참가 물질

7

반응물 4

HCID 297MethaneHCID 6228DimethylformamideHCID 11955BenzoylhydrazineHCID 587105723-Amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile

생성물 1

HCID 178508343HCID 178508343, 화합물수율 29%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
190 °C

실험 절차

A mixture of 3-amino-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carbonitrile (0.11 g, 0.5 mmol) and benzoic hydrazide (0.15 g, 1 mmol) were heated at 180-200° C. for 30 min. After cooling, the reaction mass was taken up with 5 mL DMF and the obtained solution was diluted with EtOAc and water, clarified with charcoal and filtered on Celite. The organic layer was separated. After drying over sodium sulfate, the ethyl acetate was evaporated under reduced pressure. Purification of the residue by preparative HPLC (Acetonitrile/water) gave desired product (50 mg): 1H NMR (400 MHz; DMSO-d6): 8.3 (s, 1H); 8.1 (m, 2H); 7.6-7.3 (m, 7H); 5.45 (t, 1H); 4.6 (d, 2H); MS (EI) for C23H22N5OF3 HCl: 442 (MH+).

후처리

  1. temperatureAfter cooling
  2. filtrationfiltered on Celite
  3. customThe organic layer was separated
  4. dry with materialAfter drying over sodium sulfate
  5. customthe ethyl acetate was evaporated under reduced pressure
  6. customPurification of the residue by preparative HPLC (Acetonitrile/water)

출처 및 근거

ORD 기록
ord-1d31dba7f196450bbc106bb2d5fa2cc2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

반응 노트

불러오는 중…