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Hexane → (S)-6-(2,6-diethyl-phenyl)-4-methoxy-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridine-2-carbonitrile

HRID 1392628
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HRID 1392628 반응식
Br[CH2:2][C:3]1[C:4]([C:21]#[N:22])=[N:5][C:6]([C:11]2[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:19][CH3:20])=[CH:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].[CH3:29][NH:30][C@@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1.CCCCCC>CC#N.O>[CH2:19]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][CH3:18])[C:11]=1[C:6]1[N:5]=[C:4]([C:21]#[N:22])[C:3]([CH2:2][N:30]([CH3:29])[C@@H:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34][CH2:33][CH2:32]2)=[C:8]([O:9][CH3:10])[CH:7]=1)[CH3:20]
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참가 물질

7

반응물 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 7128547(1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamineHCID 669943133-Bromomethyl-6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-2-carbonitrile

생성물 1

HCID 59678190(S)-6-(2,6-diethyl-phenyl)-4-methoxy-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridine-2-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-bromomethyl-6-(2,6-diethyl-phenyl)-4-methoxy-pyridine-2-carbonitrile (40 mg), K2CO3 (50 mg) and (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (40 mg) in CH3CN (2 mL) is stirred at room temperature overnight. Hexane (5 mL) and water (5 mL) are added to the mixture. The organic layer is separated, washed, once with brine, dried (Na2SO4), and concentrated. The crude is purified by PTLC (4:1 hexane/EtOAc) to give (S)-6-(2,6-diethyl-phenyl)-4-methoxy-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridine-2-carbonitrile. 1H NMR (CDCl3) 7.72 (d, 1H), 7.35 (t, 1H), 7.07-7.17 (m, 5H), 6.92 (s, 1H), 4.05 (m, 1H), 3.97 (d, 2H), 3.89 (s, 3H), 2.75 (m, 2H), 2.32 (m, 4H), 2.22 (s, 3H), 2.09 (m, 2H), 2.70-2.95 (m, 2H), 1.08 (t, 6H).

후처리

  1. customThe organic layer is separated
  2. washwashed, once with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude is purified by PTLC (4:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-b5a198867f724d8ea20445a1bd971f75
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342115B2

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