4-Amino-1-Boc-piperidine → Tert-butyl 4-((5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)amino)piperidine-1-carboxylate

HRID 877566Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:21]=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[C:19]([C:26]2[O:27][C:28](S(C)(=O)=O)=[N:29][N:30]=2)=[CH:18][N:17]=1>O1CCOCC1>[Cl:15][C:16]1[N:17]=[CH:18][C:19]([C:26]2[O:27][C:28]([NH:1][CH:2]3[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)=[N:29][N:30]=2)=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-butyl 4-aminopiperidine-1-carboxylate (8 mmol, 5 equiv.) was added to a stirred solution of 2-chloro-N-isopropyl-5-(5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl)pyridin-4-amine (44) (500 mg, 1.7 mmol) in Dioxan (5 mL) and heated at 90° C. for 4 h. The reaction mass was concentrated under reduced pressure. The crude material obtained was purified by column chromatography through silica gel and MeOH: DCM as eluent to afford the desired compound, tert-butyl 4-((5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)amino)piperidine-1-carboxylate. LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 2.049 min; LCMS (ES-API), m/z 437.2 (M+H).

Workup

concentrationThe reaction mass was concentrated under reduced pressure
customThe crude material obtained
customwas purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record: ord-59f7edf4b2f245f2bda3a9b6c70fea6b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987311B2

Reaction notes

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