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 251596Notes

Reaction equation

HRID 251596 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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), 2.2 (s, 3H), 2.09 (m, 2H), 2.70-2.95 (m, 2H), 1.08 (t, 6H).

Workup

  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)

Sources & evidence

ORD record
ord-465bdbccba62474cbe1e243416500eb5
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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