1,1'-Carbonyldiimidazole → HCID 58728486, compound

HRID 1992069Notes

Reaction equation

HRID 1992069 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O/[N:30]=[C:31](\[NH2:39])/[CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>CN(C=O)C>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH2:32][C:31]2[N:39]=[C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]3)[O:16][N:30]=2)[CH:34]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 9648379HCID 9648379, compound

Product 1

HCID 58728486HCID 58728486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1-(Tert-butoxycarbonyl)piperidine-4-carboxylic acid (2.29 g, 0.010 mmol) was treated with 1,1′-carbonyldiimidazole (1.62 g, 0.010 mmol) in DMF (5 mL) at ambient temperature for 30 min. Following this activation period, the crude (1Z)-N′-hydroxy-2-pyridin-3-ylethanimidamide (0.010 mmol) was added and the reaction mixture heated at 70° C. for 6 h followed by 120° C. for an additional 6 h. The reaction mixture was cooled and partitioned between EtOAc and water. The organic phase was separated, washed successively with saturated NaHCO3 and brine, dried over MgSO4, filtered and concentrated to give tert-butyl 4-[3-(pyridin-3-ylmethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate. 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.53 (m, 1H), 7.67 (d, 1H, J=7.7 Hz), 7.28 (m, 1H), 4.20-4.05 (m, 2H), 4.08 (s, 2H), 3.08 (m, 1H), 2.94 (m, 2H), 2.04 (m, 2H), 1.87-1.73 (m, 2H), 1.47 (s, 9H). ES-LCMS m/z 367.36 (M+Na).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic phase was separated
  4. washwashed successively with saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4d1a5fb02db44f0997a803419c407851
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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