Diethyl Ether → HCID 59678225, compound

HRID 1392644Notes

Reaction equation

HRID 1392644 reaction equation
[CH3:1]S(Cl)(=O)=O.[N:6]1([C:10]2[CH:15]=[C:14]([C:16]3[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:24][CH3:25])[N:13]=[C:12]([CH3:26])[C:11]=2[CH2:27]O)[CH2:9][CH2:8][CH2:7]1.[CH3:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[CH3:35][CH2:36]OCC.[CH3:40][C:41]#[N:42]>C(Cl)Cl.O>[N:6]1([C:10]2[CH:15]=[C:14]([C:16]3[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:24][CH3:25])[N:13]=[C:12]([CH3:26])[C:11]=2[CH2:27][N:42]([CH3:1])[C@@H:41]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][CH2:29][CH2:40]2)[CH2:9][CH2:8][CH2:7]1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 8058HexaneHCID 31297Methanesulfonyl chlorideHCID 58089856HCID 58089856, compound

Product 1

HCID 59678225HCID 59678225, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (114 mg, 1 mmol) is added to a solution of [4-azetidin-1-yl-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-yl]-methanol (150 mg, 0.5 mmol) and TEA (100 mg) in CH2Cl2 (2 mL). The resulting mixture is stirred at room temperature for 2 hours. The volatile material is removed in vacuo. A mixture of the resulting residue, K2CO3 (138 mg) and (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (240 mg) (prepared by the method given in Example 1) in CH3CN (4 mL) is stirred at room temperature overnight. Hexane (5 mL), ether (5 mL) and water (10 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 (10% MeOH in CH2Cl2) to give (S)-[4-azetidin-1-yl-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine. 1H NMR (CDCl3) 7.73 (d, 2H), 7.08-7.25 (m, 6H), 6.09 (s, 1H), 4.18 (t, 4H), 3.85 (m, 3H), 2.83 (m, 2H), 2.63 (s, 3H), 2.38 (m, 6H), 2.02 (m, 3H), 1.80 (m, 2H), 1.08 (t, 6H).

Workup

  1. customThe volatile material is removed in vacuo
  2. additionA mixture of the resulting residue, K2CO3 (138 mg) and (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (240 mg) (
  3. customprepared by the method
  4. stirringis stirred at room temperature overnight
  5. customThe organic layer is separated
  6. washwashed once with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude is purified by PTLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e3e65328e73f43d5903659362165a09a
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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