1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 71525483, compound

HRID 1477768Notes

Reaction equation

HRID 1477768 reaction equation
[CH3:1][C:2]([NH:10][C:11]([C:13]1[CH:18]=[N:17][C:16](Br)=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[N:14]=1)=[O:12])([C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1)[CH3:3].Cl.[F:28][C:29]1([F:33])[CH2:32][NH:31][CH2:30]1.C1CCN2C(=NCCC2)CC1>CS(C)=O>[CH3:1][C:2]([NH:10][C:11]([C:13]1[CH:18]=[N:17][C:16]([N:31]2[CH2:32][C:29]([F:33])([F:28])[CH2:30]2)=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[N:14]=1)=[O:12])([C:4]1[N:8]=[C:7]([CH3:9])[O:6][N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 86682317HCID 86682317, compound

Product 1

HCID 71525483HCID 71525483, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromo-6-(3-chloro-phenyl)-pyrazine-2-carboxylic acid [1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide (Example 1e, 0.075 g, 172 μmol) was added to a solution containing 3,3-difluoroazetidine hydrochloride (77.9 mg, 601 μmol) and DBU (91.5 mg, 89.8 μl, 601 μmol) in DMSO (1 mL). The reaction mixture was stirred at room temperature for 2 hours and extracted with ethyl acetate and 10% citric acid. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude material was purified by reverse phase chromatography to give the desired product (8 mg, 10%) as colorless oil; MS (ESI): 449.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate and 10% citric acid
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-b6815ae7ffd24a37af0d15fc02c2e133
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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