Imidazole → HCID 66811607, compound

HRID 1099206Notes

Reaction equation

HRID 1099206 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([NH:17][NH:18][C:19]([CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][CH2:24][CH2:23][N:22]2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:20])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]2[O:20][C:19]([CH:21]3[CH:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:25][CH2:24][CH2:23][N:22]3[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[N:18][N:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66811536HCID 66811536, compound

Product 1

HCID 66811607HCID 66811607, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-{[2-({1-[(benzyloxy)carbonyl]azetidin-3-yl}carbonyl)hydrazino]carbonyl}-3-phenylpiperidine-1-carboxylate (235 mg, 0.44 mmol) in dichloromethane (4 ml) at 0° C. were added imidazole (71.6 mg, 1.05 mmol), polystyrene bound triphenyl phosphine (471 mg, 0.96 mmol, 2.04 g/mmol), and carbon tetrabromide (320 mg, 0.96 mmol). The reaction was warmed to rt and allowed to stir for 18 h. The reaction mixture was filtered and rinsed with dichloromethane. The filtrate was concentrated to give an oil. The crude material was purified via flash chromatography (silica, 0-35% EtOAc/hexanes) to yield tert-butyl 2-(5-{1-[(benzyloxy)carbonyl]azetidin-3-yl}-1,3,4-oxadiazol-2-yl)-3-phenylpiperidine-1-carboxylate (96%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washrinsed with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customto give an oil
  5. customThe crude material was purified via flash chromatography (silica, 0-35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6d15d1416b67463985bfbd691c25386f
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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