Water → (S)-(6-(2,6-Diethyl-phenyl)-4-ethyl-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-YL)-amino]-methyl}-pyridin-2-YL)-methyl-amine

HRID 1392633Notes

Reaction equation

HRID 1392633 reaction equation
Cl[C:2]1[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH2:21][CH3:22])[CH:5]=[C:4]([C:23]2[C:28]([CH2:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:31][CH3:32])[N:3]=1.CN.[CH3:35][N:36]1C(=O)CCC1.O>CCCCCC>[CH2:31]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH2:29][CH3:30])[C:23]=1[C:4]1[N:3]=[C:2]([NH:36][CH3:35])[C:7]([CH2:8][N:9]([CH3:20])[C@@H:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[C:6]([CH2:21][CH3:22])[CH:5]=1)[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 59678252(S)-[2-chloro-6-(2,6-diethyl-phenyl)-4-ethyl-pyridin-3-ylmethyl]-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine

Product 1

HCID 59678153(S)-(6-(2,6-Diethyl-phenyl)-4-ethyl-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-YL)-amino]-methyl}-pyridin-2-YL)-methyl-amine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (S)-[2-chloro-6-(2,6-diethyl-phenyl)-4-ethyl-pyridin-3-ylmethyl]-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (50 mg), anhydrous MeNH2 (2 mL) and NMP (3 mL) is heated in a sealed tube at 110° C. overnight. On cooling, water (10 mL) and hexane (20 mL) are added and the organic layer is separated. The organic layer is washed with brine, dried and concentrated. The residue is purified by PTLC (8:1 Hexane/EtOAc) to give the desired product. 1H NMR (CDCl3) 7.45 (d, 1H), 7.10-7.26 (m, 6H), 6.82 (br, 1H), 6.32 (s, 1H), 3.95 (m, 1H), 3.77 (m, 2H), 2.30 (s, 3H), 2.75 (m, 2H, 2.65 (m, 2H), 2.42 (m, 4H), 2.11 (s, 3H), 1.80-2.10 (m, 2H), 1.07-1.27 (m, 9H).

Workup

  1. temperatureOn cooling
  2. customthe organic layer is separated
  3. washThe organic layer is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by PTLC (8:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-9d3466cc773a4eae99d2f4532bff9b74
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

Loading…