Triethylamine → HCID 59678370, compound

HRID 251591Notes

Reaction equation

HRID 251591 reaction equation
CS(Cl)(=O)=O.[CH2:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C.[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH3:22])[C:16]=1[C:23]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])C(CO)=[C:25]([O:35][CH3:36])[CH:24]=1)[CH3:14].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(OCC)(=O)C.O.C(#N)C>[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH3:22])[C:16]=1[C:23]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[C:10]([CH2:9][N:8]([CH3:6])[C@@H:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:13][CH:14]=3)[CH2:18][CH2:19][CH2:20]2)=[C:25]([O:35][CH3:36])[CH:24]=1)[CH3:14]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 59678353HCID 59678353, compound

Product 1

HCID 59678370HCID 59678370, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.42 g, 3.7 mmol) and triethylamine (0.37 g, 3.7 mmol) are added to a solution of [6-(2,6-diethyl-phenyl)-4-methoxy-2-trifluoromethyl-pyridin-3-yl]-methanol (1.0 g, 3.0 mmol) in DCM (1 mL) and the mixture is stirred at room temperature for 1 hour. The volatile material is removed in vacuo. K2CO3 (1.3 g, 9.3 mmol), (S)-methyl-(1,2,3,4-naphthalen-1-yl)-amine (1.5 g, 9.3 mmol), and acetonitrile (20 mL) are added to the residue. The mixture is stirred at room temperature for 16 hours. The reaction is diluted with ethyl acetate (20 mL) and water (20 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 mL). The combined organic layers are dried and solvent removed. The crude product is purified by PTLC (hexanes/ethyl acetate 6:1) to give (S)-[6-(2,6-diethyl-phenyl)-4-methoxy-2-trifluoromethyl-pyridin-3-ylmethyl]-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine. 1H NMR: (CDCl3) 7.68 (d, 1H), 7.29 (m, 1H), 7.12 (m, 5H), 6.95 (S, 1H), 4.04 (m, 3H), 3.91 (s, 3H), 2.76 (m, 2H), 2.35 (m, 4H), 2.06 (m, 5H), 1.80 (m, 2H), 1.07 (t, 6H). [α]D=+10.7 (16.7 mg/l mL benzene).

Workup

  1. customThe volatile material is removed in vacuo
  2. stirringThe mixture is stirred at room temperature for 16 hours
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with ethyl acetate (2×20 mL)
  5. customThe combined organic layers are dried
  6. customsolvent removed
  7. customThe crude product is purified by PTLC (hexanes/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-3cc02435c0ad4e7aaef27b257fee2b7c
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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