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

HRID 1713141ノート

反応式

HRID 1713141 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f8e9205dc2ce46b09e081bf008ee17d4
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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