Ethyl 4-piperidinecarboxylate → HCID 69207088, compound

HRID 2376634Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:6]=[CH:7][CH:8]=1.[NH:27]1[CH2:37][CH2:36][CH:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:29][CH2:28]1>CS(C)=O>[CH2:34]([O:33][C:31]([CH:30]1[CH2:36][CH2:37][N:27]([C:11]2[CH:12]=[C:13]3[C:18](=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=4)[N:10]=2)[N:17]=[CH:16][CH:15]=[CH:14]3)[CH2:28][CH2:29]1)=[O:32])[CH3:35]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 8-(3-methylsulfanyl-phenyl)-[1,7]naphthyridin-6-yl ester (160 mg, 0.4 mmol) in DMSO (1 ml) is added ethyl isonipecotate (138 mg). The solution is stirred at 60° C. for 23 hours and then partitioned between ethyl acetate and water. The organic layer is separated and washed with brine 3×., then dried over magnesium sulfate and concentrated. The crude product is purified by flash chromatography on silica gel, eluting with 8% isohexane:DCM, increasing polarity to 2% methanol:DCM. The product is obtained as an amorphous solid. MS (ES+) 408.0893

Workup

custompartitioned between ethyl acetate and water
customThe organic layer is separated
washwashed with brine 3×
dry with material, then dried over magnesium sulfate
concentrationconcentrated
customThe crude product is purified by flash chromatography on silica gel
washeluting with 8% isohexane
temperatureDCM, increasing polarity to 2% methanol
customThe product is obtained as an amorphous solid

Sources & evidence

ORD record: ord-3c95f843e0f844e6bb4932b3e1671bd6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468370B2

Reaction notes

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