HCID 59457665, compound → HCID 59457731, compound

HRID 2193744Notes

Reaction equation

HRID 2193744 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH:15]=3)[S:13][C:6]=12>C(Cl)Cl>[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH:15]=3)[S:13][C:6]=12

Participants

3

Reactant 1

HCID 59457665HCID 59457665, compound

Product 1

HCID 59457731HCID 59457731, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 267 (1 g, 2.13 mmol) in DCM (4.3 mL) TFA (4.3 mL) was added and the reaction mixture was stirred for 2 h at room temperature. The solvent was removed under reduced pressure, the residue was suspended in aqueous sodium bicarbonate, the mixture extracted with DCM, EtOAc and DCM; the combined organic phases were filtered and the recovered solids dried. The organic phase was dried over anhydrous Na2SO4, concentrated under reduced pressure and the residue was combined with the solid material obtained earlier to provide 268 (806 mg, 2.12 mmol, 100% yield) as a yellow solid. MS (m/z): (M+1) 372.1 (100%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe mixture extracted with DCM, EtOAc and DCM
  3. filtrationthe combined organic phases were filtered
  4. customthe recovered solids dried
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customobtained earlier

Sources & evidence

ORD record
ord-11359c2700b5458fb314039d2cc75d7c
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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