Potassium Carbonate → HCID 58902343, compound

HRID 1640177Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:35])[CH2:33]Cl)[CH:26]=4)=[CH:19][CH:20]=3)[CH:15]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:35])[CH2:33][N:46]5[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]5)[CH:26]=4)=[CH:19][CH:20]=3)[CH:15]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of N-(3-tert-butylphenyl)-7-({2-[(chloroacetyl)amino]pyridin-4-yl}oxy)-2-naphthamide (65.0 mg, 0.133 mmol) and potassium carbonate (36.8 mg, 0.266 mmol) in DMF (2 mL) was added 1-methylpiperazine (0.177 mL, 0.160 mmol). The reaction mixture was allowed to stir at 60° C. for 2 h. and then concentrated. EtOAc and water were added and the organic and aqueous solutions were separated. The organic solution was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-(3-tert-butylphenyl)-7-[(2-{[(4-methylpiperazin-1-yl)acetyl]-amino}pyridin-4-yl)oxy]-2-naphthamide I-264 ( ) (33 mg, 37%).

Workup

concentrationconcentrated
additionEtOAc and water were added
customthe organic and aqueous solutions were separated
washThe organic solution was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-d78baba1d02849a09a87f7b393ba2ead
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110687B2

Reaction notes

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