3,3-Dimethylbutylamine → HCID 178444849, compound

HRID 1925555Notes

Reaction equation

HRID 1925555 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[SH:32][C:33]1[N:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=O.[CH3:42][C:43]([CH3:48])([CH3:47])[CH2:44][CH2:45][NH2:46]>CN(C=O)C.CCCCCC.CC(C)=O>[CH3:42][C:43]([CH3:48])([CH3:47])[CH2:44][CH2:45][NH:46][C:35](=[O:37])[C:34]1[CH:38]=[CH:39][CH:40]=[N:41][C:33]=1[SH:32]

Participants

7

Reactant 4

HCID 197093,3-DimethylbutylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178524460HCID 178524460, compound

Product 1

HCID 178444849HCID 178444849, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21880519Acetone hexaneSolvent

Conditions

Temperature
0 °C

Procedure

5.84 ml (33.8 mmol) of DIPEA and 4.66 g (14.5 mmol) of TBTU were added at 0° C. to a solution of 1.50 g (9.7 mmol) of 2-mercapto-nicotinic acid in DMF (30 ml). After stirring for 30 min at 0° C., 1.6 ml (11.6 mmol) of 3,3-dimethylbutan-1-amine were added and then the mixture was stirred for 16 h at RT. Dilution with water (100 ml) and extraction with EA (2×100 ml) were then carried out. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/acetone 1:1) of the residue yielded 1.4 g (5.9 mmol, 61%) of N-(3,3-dimethylbutyl)-2-mercapto-nicotinamide.

Workup

  1. stirringthe mixture was stirred for 16 h at RT
  2. extractionDilution with water (100 ml) and extraction with EA (2×100 ml)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-297417724d7d44f6981ceb5d5aa251a6
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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