Acetohydrazide → 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

HRID 1485375노트

반응식

HRID 1485375 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=S)[NH:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1.[C:21]([NH:24][NH2:25])(=O)[CH3:22]>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12]3=[N:25][N:24]=[C:21]([CH3:22])[N:11]3[C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14039AcetohydrazideHCID 867184911-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

생성물 1

HCID 709795286-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one수율 40.1%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1.0 g, 3.3 mmol) and acetohydrazide (1.23 g, 16.6 mmol) in n-butanol (20 ml) was refluxed for 24 h under N2 atmosphere. The solvent was evaporated in vacuo and partitioned between DCM (100 mL) and water (50 mL). The organic phase was dried over Na2SO4 and the solvent was evaporated in vacuo to afford a residue. The residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1) to give 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (430.0 mg, 40%). LRMS (M+H+) m/z: calcd 324.08. found 324. 1H NMR (300 MHz, CD3OD): δ 2.72 (s, 3H), 3.94 (q, J=14.1 Hz, 2H), 7.15-7.24 (m, 3H), 7.40-7.52 (m, 4H), 7.70-7.73 (m, 1H).

후처리

  1. customThe solvent was evaporated in vacuo
  2. custompartitioned between DCM (100 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customto afford a residue
  6. customThe residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1)

출처 및 근거

ORD 기록
ord-ec9d33ff21eb4d0895cb1a342376606d
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422292B2

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