1,1'-Carbonyldiimidazole → HCID 67516007, compound

HRID 2038789Notes

Reaction equation

HRID 2038789 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.O[NH:34][C:35]([CH:37]1[CH2:39][CH2:38]1)=[NH:36]>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]3[O:18][N:36]=[C:35]([CH:37]4[CH2:39][CH2:38]4)[N:34]=3)=[CH:14][N:13]=2)[CH2:10][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 67508334HCID 67508334, compoundHCID 178513214HCID 178513214, compound

Product 1

HCID 67516007HCID 67516007, compoundYield 380%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(1-tert-butoxycarbonylamino-cyclopropyl)-nicotinic acid (0.10 g, 0.10 mmol) in DMF (5 mL) was added CDI (0.16 g, 0.10 mmol). The mixture was stirred at room temperature for 3 h. N-hydroxy-cyclopropanecarboxamidine (0.28 g, 0.10 mmol) was then added and the reaction mixture heated at 100° C. for 24 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, satd aqueous NaHCO3, brine and dried with MgSO4. The mixture was filtered and concentrated to give {1-[5-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-pyridin-2-yl]-cyclopropyl}-carbamic acid tert-butyl ester (0.13 g, 0.38 mmol) as a yellow oil, m/z 343.7 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated at 100° C. for 24 h
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined extracts were washed with water
  5. dry with materialdried with MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0bc04dc1bb8247429d438af074fbc4ec
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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