Potassium Carbonate → (2,6-Dichloro-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-4-yl)-pyrrolidin-1-yl-methanone

HRID 1392671Notes

Reaction equation

HRID 1392671 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[C:6]([C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1.O=S(Cl)Cl.C([O-])([O-])=O.[K+].[K+].[CH3:28][NH:29][C@@H:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH2:31]1>C(Cl)Cl.O.CCOC(C)=O.CC#N>[Cl:1][C:2]1[C:7]([CH2:8][N:29]([CH3:28])[CH:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][CH2:32][CH2:31]2)=[C:6]([C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 7128547(1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamineHCID 59678084(2,6-Dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone

Product 1

HCID 72355817(2,6-Dichloro-3-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyridin-4-yl)-pyrrolidin-1-yl-methanone

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2,6-dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone (400 mg, 1.45 mmol) and SOCl2 (1 mL) in CH2Cl2 (10 mL) is stirred at room temperature for 1 hour, and then concentrated. The residue is treated with K2CO3 (1.0 g, 7.2 mmol), CH3CN (10 mL) and (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (250 mg, 1.55 mmol). The resulting mixture is stirred at room temperature overnight. EtOAc (50 mL) and water (40 mL) are added to the residue. The organic layer is separated, washed once with brine, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (4:1 hexane:EtOAc) to give the title compound.

Workup

  1. concentrationconcentrated
  2. stirringThe resulting mixture is stirred at room temperature overnight
  3. customThe organic layer is separated
  4. washwashed once with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (4:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-b544b6264dce40f6b70173e666811b95
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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