4-Methylmorpholine → N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide

HRID 1925550Notes

Reaction equation

HRID 1925550 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[SH:30][C:31]1[N:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([OH:35])=O.[CH:40]12[CH2:46][CH:43]([CH2:44][CH2:45]1)[CH2:42][CH:41]2[CH2:47][NH2:48]>CN(C=O)C.CC(=O)OCC.C(Cl)Cl.CO>[CH:40]12[CH2:46][CH:43]([CH2:44][CH2:45]1)[CH2:42][CH:41]2[CH2:47][NH:48][C:33](=[O:35])[C:32]1[CH:36]=[CH:37][CH:38]=[N:39][C:31]=1[SH:30]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 97761Bicyclo(2.2.1)heptane-2-methanamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178524460HCID 178524460, compound

Product 1

HCID 178522760N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamideYield 53%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4.82 g (15.0 mmol) of TBTU and 3.54 g (35 mmol) of N-methyl-morpholine were added to a solution of 1.55 g (10.0 mmol) of 2-mercapto-nicotinic acid in DMF (30 ml), and the mixture was stirred for 30 min at RT. 1.25 g (10.0 mmol) of bicyclo-[2.2.1]heptan-2-ylmethanamine were then added, and stirring was carried out for 16 h at RT. The mixture was then diluted with EA and washed with sat. aq. NH4Cl sol., a 1N aq. NaHCO3 sol. and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (DCM/MeOH 99:1) of the residue yielded 308 mg 1.39 g (5.3 mmol, 53%) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide.

Workup

  1. stirringstirring
  2. waitwas carried out for 16 h at RT
  3. washwashed with sat. aq. NH4Cl sol.
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c4968481044434b9e3ec3b4ba86b86d
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

Loading…