4-Amino-1-Boc-piperidine → tert-Butyl 4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidine-1-carboxylate

HRID 1713875Notes

Reaction equation

HRID 1713875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([O:16]CC)=O)=[N:11][N:10]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:32][CH:29]2[CH2:28][CH2:27][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:31][CH2:30]2)=[O:16])=[N:11][N:10]=1

Participants

3

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 59464107Ethyl 5-[(2-fluorophenyl)amino]-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 59464243tert-Butyl 4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidine-1-carboxylateYield 74%

Procedure

(intermediate 40) (102 mg, 0.41 mmol) and tert-butyl-4-aminopiperidine-1-carboxylate (81 mg, 0.41 mmol) was heated to 85° C. for 18 hours. Upon cooling the solid was filtered and washed with EtOH (10 mL), Et2O (10 mL) then hexane (10 mL) to leave the title compound (123 mg, 74%) as a white solid; 1H NMR δ 1.41 (9H, s), 1.46-1.54 (2H, m), 1.73-1.76 (2H, m), 2.81 (2H, s), 3.93-3.96 (3H, m), 7.13-7.17 (1H, m), 7.23-7.32 (2H, m), 7.99-8.04 (1H, m), 9.02 (1H, d), 10.63 (1H, s); MS m/e (M−H)− 404.

Workup

  1. temperatureUpon cooling the solid
  2. filtrationwas filtered
  3. washwashed with EtOH (10 mL), Et2O (10 mL)

Sources & evidence

ORD record
ord-851defe4f0cf488eb0acd5e1223f5c97
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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