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 251601Notes

Reaction equation

HRID 251601 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-952d4acc8dc54beb9a08a87983411395
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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