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 1392628Notes

Reaction equation

HRID 1392628 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), 2.22 (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-b5a198867f724d8ea20445a1bd971f75
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

Loading…