Potassium Carbonate → 1,1-Dimethylethyl [1-(2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate

HRID 656959Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-chloro-6-(methyloxy)-3-nitropyridine (1.9 g, 10 mmol), 1,1-dimethylethyl [1-(2-aminoethyl)-4-piperidinyl]carbamate (2.43 g, 10 mmol) and potassium carbonate (1.4 g, 10 mmol) in acetonitrile (35 ml) and DMF (10 ml) was heated at 40° C. for 30 minutes. The mixture was filtered, washing with acetonitrile, and evaporated. The residue was dissolved in the minimum volume of DCM (15 ml) and washed with water (1 ml). The organic extract was added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording a yellow solid (3.1 g, 78%).

Workup

filtrationThe mixture was filtered
washwashing with acetonitrile
customevaporated
dissolutionThe residue was dissolved in the minimum volume of DCM (15 ml)
washwashed with water (1 ml)
extractionThe organic extract
additionwas added to a silica column which
washwas then eluted with 0-100% ethyl acetate in hexane affording a yellow solid (3.1 g, 78%)

Sources & evidence

ORD record: ord-4336fff4f65f4f8da1afcf7bcc85738e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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