Sodium Iodide → 7-[2-(4-Bromophenyl)ethyl]-2-(3,5-dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione

HRID 49984

반응식

HRID 49984 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]Br)=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([N:19]2[C:27](=[O:28])[CH:22]3[CH2:23][NH:24][CH2:25][CH2:26][N:21]3[C:20]2=[O:29])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:24]2[CH2:25][CH2:26][N:21]3[C:20](=[O:29])[N:19]([C:14]4[CH:15]=[C:16]([Cl:18])[CH:17]=[C:12]([Cl:11])[CH:13]=4)[C:27](=[O:28])[CH:22]3[CH2:23]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 110108254-Bromophenethyl bromideHCID 213010012-(3,5-Dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione

생성물 1

HCID 213010147-[2-(4-Bromophenyl)ethyl]-2-(3,5-dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione

시약·촉매·용매 1

HCID 112513-Methyl-2-butanone용매

실험 절차

A mixture of 1-bromo-4-(2-bromoethyl)benzene (101 mg, 0.38 mmol, prepared as described in Synth.Commun [1996], 26, pp. 1467-1472), 2-(3,5-dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione (100 mg, 0.33 mmol, Prep. 19), potassium carbonate (48 mg, 0.35 mmol) and sodium iodide (10 mg, 0.06 mmol) in methyl isopropyl ketone (2 mL) was heated at 100° C. for 48 h. The precipitate was discarded and the filtrate was concentrated under vacuum and chromatographed over silica gel (CH2Cl2). The obtained oil was treated with Et2O/HCl to yield the hydrochloride of 7-[2-(4-bromophenyl)ethyl]-2-(3,5-dichlorophenyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione as a white solid (60 mg). 1H NMR (CDCl3) of the free base: 7.25-7.4 (5H, m), 7.00 (2H, d, J=8.3Hz), 4-4.15 (2H, m), 3.32 (1H, dd, J1=4.1 Hz, J2=11.1 Hz), 3.09 (1H, dt), 2.87 (1H, br d), 2.5-2.8 (4H, m), 1.95-2.15 (2H, m)

후처리

  1. customprepared
  2. concentrationthe filtrate was concentrated under vacuum
  3. customchromatographed over silica gel (CH2Cl2)
  4. additionThe obtained oil was treated with Et2O/HCl

출처 및 근거

ORD 기록
ord-6e78110cbfb549ef9b67c2bbe72dedd0
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

연결된 노트

불러오는 중…