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

HRID 1925547Notes

Reaction equation

HRID 1925547 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][NH2:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[SH:41][C:42]1[N:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](O)=[O:45]>C1COCC1.CC(=O)OCC>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][NH:9][C:44](=[O:45])[C:43]1[CH:47]=[CH:48][CH:49]=[N:50][C:42]=1[SH:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 97761Bicyclo(2.2.1)heptane-2-methanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524460HCID 178524460, compound

Product 1

HCID 178522760N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamideYield 50.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g (40.0 mmol) of bicyclo[2.2.1]heptan-2-ylmethanamine, 16.0 g (42.0 mmol) of HATU and 5.8 ml (42.0 mmol) of NEt3 were added in succession to a solution of 6.2 g (40.0 mmol) of 2-mercapto-nicotinic acid in THF (320 ml), and the mixture was stirred for 4 d at RT. Dilution with EA was then carried out. The organic phase was separated off, washed with a 1M aq. Na2CO3 sol. and a 4M aq. NH4Cl sol., dried over MgSO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3→1:1→3:7) was carried out with the residue. The resulting prepurified product was dissolved in 1N aq. NaOH (100 ml) and the solution was washed with ether. The aqueous phase was adjusted to pH ˜2 with 2M hydrochloric acid. The resulting precipitate was filtered off and then washed with pentane and dried in vacuo. 5.3 g (20.2 mmol, 50%) of N-(bicyclo[2.2.1]heptan-2-ylmethyl)-2-mercapto-nicotinamide were obtained.

Workup

  1. customThe organic phase was separated off
  2. washwashed with a 1M aq. Na2CO3 sol.
  3. dry with materiala 4M aq. NH4Cl sol., dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting prepurified product was dissolved in 1N aq. NaOH (100 ml)
  7. washthe solution was washed with ether
  8. filtrationThe resulting precipitate was filtered off
  9. washwashed with pentane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-8ea66353ad7243339ce34a5859c5995e
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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