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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
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HRID 2365406 반응식
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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-bd205d17aae94dac8ef1ce281b60bff8
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697700B2

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