1,1'-Carbonyldiimidazole → HCID 90203654, compound

HRID 624974Notes

Reaction equation

HRID 624974 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[C:19](O)=[O:20])=[O:13])[CH:9]=[CH:8][C:7]=2[N:22]2[CH2:25][C:24]([F:27])([F:26])[CH2:23]2)[CH2:3][CH2:2]1.C(N1C=CN=C1)([N:30]1C=CN=C1)=O>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[C:19]([NH2:30])=[O:20])=[O:13])[CH:9]=[CH:8][C:7]=2[N:22]2[CH2:23][C:24]([F:27])([F:26])[CH2:25]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 90203642HCID 90203642, compound

Product 1

HCID 90203654HCID 90203654, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 1-(6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinoyl)pyrrolidine-2-carboxylic acid (8.6 mg, 22.6 μmol) in DMF (2 mL) was added carbonyldiimidazole (10.2 mg, 63.1 μmol). After 5 minutes the reaction mixture was warmed to ambient temperature and stirred for 2 h. NH3 gas was bubbled through the solution for 10 minutes and stirring was continued for 12 h. The reaction mixture was poured onto ice-water (20 mL) and extracted with EtOAc (2×20 mL). The combined extracts were dried over Na2SO4 and concentrated in vacuo to give the title compound (9 mg, quant.) as colorless wax; MS (EI): m/e=381.5 [MH+].

Workup

  1. customNH3 gas was bubbled through the solution for 10 minutes
  2. stirringstirring
  3. waitwas continued for 12 h
  4. additionThe reaction mixture was poured onto ice-water (20 mL)
  5. extractionextracted with EtOAc (2×20 mL)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e1cc3c11fbe4125aab6f07d81b786ad
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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