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 595499Notes

Reaction equation

HRID 595499 reaction equation
N1(C([O-])=O)CCCCC1.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[Cl:24][C:25]1[CH:30]=[C:29]([NH:31][CH:32]([CH3:34])[CH3:33])[C:28]([C:35]2[O:36][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[N:38][N:39]=2)=[CH:27][N:26]=1>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[C:29]([NH:31][CH:32]([CH3:34])[CH3:33])[C:28]([C:35]2[O:36][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[N:38][N:39]=2)=[CH:27][N:26]=1.[Cl:24][C:25]1[N:26]=[CH:27][C:28]([C:35]2[O:36][C:37]([NH:10][CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]3)=[N:38][N:39]=2)=[C:29]([NH:31][CH:32]([CH3:34])[CH3:33])[CH:30]=1

Participants

6

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 21874245Piperidine carboxylateHCID 896910512-chloro-N-isopropyl-5-(5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

Product 2

HCID 89690937Tert-butyl 4-((5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)amino)piperidine-1-carboxylateHCID 896910512-chloro-N-isopropyl-5-(5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl)pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Synthesis of tert-butyl 445-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)amino)piperidine-1-carboxylate (45): 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

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

Sources & evidence

ORD record
ord-e9e8379347304d4ca42734ee7fb584d3
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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