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Sodium triacetoxyborohydride → 6-(2-{4-[2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}ethyl)pyridine-3-carbonitrile

HRID 1466179
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인쇄 미리보기

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HRID 1466179 반응식
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH2:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1.[CH3:18][C:19]1[C:27]2[CH2:26][O:25][C:24](=[O:28])[C:23]=2[CH:22]=[CH:21][C:20]=1[CH2:29][CH:30]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:18][C:19]1[C:27]2[CH2:26][O:25][C:24](=[O:28])[C:23]=2[CH:22]=[CH:21][C:20]=1[CH2:29][CH2:30][N:6]1[CH2:5][CH2:4][N:3]([CH2:8][CH2:9][C:10]2[N:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[C:2](=[O:1])[CH2:7]1
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참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 772312602-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 895247896-[2-(2-Oxopiperazin-1-yl)ethyl]pyridine-3-carbonitrile

생성물 1

HCID 895334956-(2-{4-[2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}ethyl)pyridine-3-carbonitrile

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

A mixture of 6-[2-(2-Oxopiperazin-1-yl)ethyl]pyridine-3-carbonitrile [I-14](1 eq), (4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (1 eq) and NaBH(OAc)3 in 10 mL of DCM was stirred overnight at RT. The mixture was diluted with 50 mL of DCM and washed with brine, concentrated and the residue was purified by prep-TLC (DCM:MeOH=15:1) to afford the title product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.73 (s, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 5.18 (s, 2H), 3.71 (t, J=7.2 Hz, 2H), 3.26 (s, 2H), 3.08-3.14 (m, 4H), 2.85 (t, J=7.6 Hz, 2H), 2.65 (s, 2H), 2.54 (t, J=7.6 Hz, 2H), 2.21 (s, 3H).

후처리

  1. washwashed with brine
  2. concentrationconcentrated
  3. customthe residue was purified by prep-TLC (DCM:MeOH=15:1)

출처 및 근거

ORD 기록
ord-12f77e2354264d6aae8d51029ab48a7c
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999990B2

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