Sodium cyanoborohydride → rac-2-(4-ethyl-1H-imidazol-1-yl)-9-(1-hydroxyethyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 532953노트

반응식

HRID 532953 반응식
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][N:16]=[C:15]([N:20]3[CH:24]=[C:23]([CH2:25][CH3:26])[N:22]=[CH:21]3)[CH:14]=[C:9]12)(=[O:3])[CH3:2].[BH3-]C#N.[Na+]>CO.C(Cl)Cl>[CH2:25]([C:23]1[N:22]=[CH:21][N:20]([C:15]2[CH:14]=[C:9]3[C:10]4[C:5]([CH2:6][CH2:7][N:8]3[C:18](=[O:19])[CH2:17][N:16]=2)=[C:4]([CH:1]([OH:3])[CH3:2])[CH:13]=[CH:12][CH:11]=4)[CH:24]=1)[CH3:26]

참가 물질

5

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 867113959-acetyl-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

생성물 1

HCID 73336024rac-2-(4-ethyl-1H-imidazol-1-yl)-9-(1-hydroxyethyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one수율 4.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Example 115. A solution of 9-acetyl-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (210 mg, 0.36 mmol) in MeOH (20 mL) was treated with NaBH3CN (23 mg, 0.36 mmol) and the mixture was stirred at RT for 10 min. The mixture was then concentrated in vacuo and the residue obtained was taken up in DCM and washed with H2O. The org layer was then dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 85:15) and preparative TLC (SiO2, DCM/MeOH 95:5) afforded the title compound (6 mg). UPLC-MS: MS 351.2 (M+H+); UPLC rt 0.65 min. 1H NMR (400 MHz, CD3OD): δ ppm 1.16-1.27 (m, 3 H); 1.44 (d, J=6.26 Hz, 3 H); 2.58 (q, J=7.56 Hz, 2 H); 2.97-3.17 (m, 2 H); 3.80 (m, 1 H); 3.88-4.00 (m, 2 H); 4.31-4.36 (m, 2 H); 5.14 (d, J=6.65 Hz, 1 H); 6.95 (s, 1 H); 7.34 (s, 1 H); 7.37-7.49 (m, 1 H); 7.67 (d, J=7.43 Hz, 1 H); 7.77 (d, J=7.82 Hz, 1 H); 8.11 (s, 1 H).

후처리

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue obtained
  3. washwashed with H2O
  4. dry with materialThe org layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 85:15) and preparative TLC (SiO2, DCM/MeOH 95:5)

출처 및 근거

ORD 기록
ord-eca669e8590c42ed95083da781f3caf9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853203B2

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