Potassium Carbonate → HCID 59401308, compound

HRID 2060853Notes

Reaction equation

[CH3:1][CH:2]([CH3:18])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[OH:17].Cl[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][CH:2]([CH3:18])[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[O:17][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-[(3-methylbutylamino)methyl]naphthalen-1-ol (Preparation 14) (85 mg, 0.35 mmol) in DMF (10 mL), was added 6-chloronicotinonitrile (43 mg, 0.62 mmol) and K2CO3 (86 mg, 0.62 mmol). The reaction mixture was heated at 70° C. for 16 h. Solvent was removed in vacuo and residue partitioned between EtOAc (50 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (50 mL) and the organic phase washed with NaHCO3 (20 mL), brine (20 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (DCM:MeOH:NH4OH, 95:5:0.5) to give the title compound: RT=2.83 min; m/z (ES+)=346.0 [M+H]+.

Workup

customSolvent was removed in vacuo and residue
custompartitioned between EtOAc (50 mL) and water (20 mL)
extractionThe aqueous phase was extracted with EtOAc (50 mL)
washthe organic phase washed with NaHCO3 (20 mL), brine (20 mL)
dry with materialdried (MgSO4)
customSolvent was removed in vacuo
customthe residue purified by column chromatography (DCM:MeOH:NH4OH, 95:5:0.5)

Sources & evidence

ORD record: ord-3c6fc398fcc24e18a8d4bd9e9e2a8a6d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278442B2

Reaction notes

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