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Acetyl chloride → 1-(2-Acetyl-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one

HRID 2365406
ノート
印刷プレビュー

反応式

HRID 2365406 の反応式
Cl.Cl.[CH3:3][N:4]1[C:12]2[CH:11]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15][C:14]3=[O:27])[CH:9]=[CH:8][C:7]=2[C:6]2[CH2:28][NH:29][CH2:30][CH2:31][C:5]1=2.[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:32]([N:29]1[CH2:30][CH2:31][C:5]2[N:4]([CH3:3])[C:12]3[CH:11]=[C:10]([N:13]4[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:15][C:14]4=[O:27])[CH:9]=[CH:8][C:7]=3[C:6]=2[CH2:28]1)(=[O:34])[CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 521913N,N-Diethyl-2-propanamineHCID 679694221-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochloride

生成物 1

HCID 573833361-(2-Acetyl-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(5-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-phenethylpiperazin-2-one dihydrochloride (170 mg, 0.368 mmol), acetyl chloride (˜120 μL, 1.5 mmol) and i-PrNEt2 (400 μL, 2.23 mmol) were combined in methylene chloride (20 mL) and stirred for 16 h. Sodium bicarbonate solution (4 mL) was added and the organics removed and concentrated. The residue was purified by flash chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 85% methylene chloride over 30 min) to provide the title compound as a white solid; 1H NMR (500 MHz, DMSO-d6) δ 11.86 (m, 1H), 7.50-7.48 (dd, J=8.3, 5.0 Hz, 1H), 7.40-7.31 (m, 5H), 7.31-7.26 (m, 1H), 6.98-6.95 (overlapping ddd, J=4.0, 1.5 Hz, 1H), 4.65 (d, J=11.2 Hz, 2H), 4.23-3.97 (m, 3H), 3.97-3.75 (m, 3H), 3.64-3.61 (m, 3H), 3.57-3.42 (m, 4H), 3.19-3.08 (m, 2H), 2.93-2.87 (m, 1H), 2.82-2.77 (m, 1H), 2.13-2.11 (2×s, 3H); ESI MS m/z 431 [M+H]+; HPLC (Method B)>99% (AUC), tR=13.8 min.

後処理

  1. customthe organics removed
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (12 g ISCO column
  4. washeluting with methylene chloride

出典と根拠

ORDレコード
ord-bd205d17aae94dac8ef1ce281b60bff8
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08697700B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート