tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate → (S)-2-[(6,7-Difluoro-3-methylquinoxaline-2-ylamino)methyl]-piperidine-1-carboxylic acid tert butylester

HRID 18084

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.14 g), and 2-chloro-6,7-difluoro-3-methylquinoxaline Teng et al PCT Int. Appl (2000), WO00/42026A1 20000720 (1.14 g) were dissolved in DMF (2 ml) and heated to 90° C. for 3 days under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 10 to 50% ethyl acetate in hexane. The title compound was obtained as a pink foam (0.524 g), MH+ 393.

Workup

temperatureAfter cooling
customthe reaction solution was partitioned between ethyl acetate and water
washThe organic layer was washed with water, saturated brine
customdried
customevaporated
customThe residue was chromatographed over silica gel
washeluting with a gradient of 10 to 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-e387087c8a394279bd035d0d571cc60a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741329B2

Linked notes

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