Sodium Iodide → 6-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine

HRID 1713141노트

반응식

HRID 1713141 반응식
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[CH2:7][NH:8][CH2:9][CH2:10][C:2]=12.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH:29]2[CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=[O:22]>C(#N)C.C(Cl)Cl>[CH:29]1([N:26]2[CH2:27][CH2:28][N:23]([C:21](=[O:22])[CH2:20][N:8]3[CH2:9][CH2:10][C:2]4[C:3](=[N:4][CH:5]=[CH:6][N:1]=4)[CH2:7]3)[CH2:24][CH2:25]2)[CH2:32][CH2:31][CH2:30]1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 552655945H,6H,7H,8H-pyrido[3,4-b]pyrazineHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazine

생성물 1

HCID 574207226-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine (70 mg, 0.518 mmol), NaI (50 mg, 0.333 mmol), and K2CO3 (200 mg, 1.45 mmol) in acetonitrile is added 2-chloro-1-(4-cyclobutyl-piperazin-1-yl)-ethanone (112 mg, 0.518 mmol). The mixture is stirred overnight at rt, diluted with DCM (20 mL) and filtered through Celite. The filtrate is evaporated and the crude product is purified by silica gel chromatography eluting with EtOAc/MeOH/NEt3 (95:5:5) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ 8.35 (2H, dd), 3.85 (2H, s), 3.70-3.66 (m, 4H), 3.46 (2H, s), 3.09 (2H, t), 2.96 (2H, t), 2.75 (1H, m), 2.37-2.34 (4H, m), 2.09-1.67 (m, 6H); MS (+VE) m/z 316.21 (M++1).

후처리

  1. filtrationfiltered through Celite
  2. customThe filtrate is evaporated
  3. customthe crude product is purified by silica gel chromatography
  4. washeluting with EtOAc/MeOH/NEt3 (95:5:5)

출처 및 근거

ORD 기록
ord-f8e9205dc2ce46b09e081bf008ee17d4
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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