Potassium Carbonate → N-(6-(1-(2-aminoethyl)-6-oxo-1,6-dihydropyridin-3-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 869991Notes

Reaction equation

[F:1][C:2]1([F:31])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([C:24]5[CH:29]=[CH:28][C:27](=[O:30])[NH:26][CH:25]=5)[N:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.Br[CH2:33][CH2:34][NH:35]C(=O)OCCCC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:35][CH2:34][CH2:33][N:26]1[C:27](=[O:30])[CH:28]=[CH:29][C:24]([C:19]2[N:18]=[C:17]([NH:16][C:14]([C:11]3([C:9]4[CH:8]=[CH:7][C:5]5[O:6][C:2]([F:1])([F:31])[O:3][C:4]=5[CH:10]=4)[CH2:13][CH2:12]3)=[O:15])[CH:22]=[CH:21][C:20]=2[CH3:23])=[CH:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask containing 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide (0.13 g, 0.3 mmol), ten-butyl 2-bromoethylcarbamate (0.35 g, 1.6 mmol), and potassium carbonate (0.5 g, 3.1 mmol) was added N,N-dimethylformamide (5 mL) and the reaction mixture was heated to 100° C. for 2 hours. The reaction was purified by reverse-phase preparative liquid chromatography to give the product (24 mg, 17%). ESI-MS m/z calc. 468.16. found 469.5 (M+1)+ Retention time 1.37 minutes.

Workup

customThe reaction was purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record: ord-04f7c2a1236e4484b358c45671956ec7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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