Triethylamine → HCID 59678370, compound

HRID 1392623Notes

Reaction equation

HRID 1392623 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/1 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-b50da6b4b8c548619cdd9d43197fa9e0
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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