3-Aminopropionitrile → Methyl 3-((2-cyanoethyl)carbamoyl)benzoate

HRID 1171499Notes

Reaction equation

HRID 1171499 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:38][CH2:39][CH2:40][C:41]#[N:42].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[C:39]([CH2:40][CH2:41][NH:42][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:10])#[N:38]

Participants

8

Reactant 4

HCID 16473-AminopropionitrileHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 21075152Methyl 3-((2-cyanoethyl)carbamoyl)benzoateYield 88.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(methoxycarbonyl)benzoic acid (800 mg, 4.4 mmol) in DMF (15 mL) at rt was added HATU (2 g, 5.3 mmol), 3-aminopropanenitrile (0.33 mL, 4.4 mmol), and iPr2NEt (0.92 mL, 5.3 mmol). The mixture was stirred at rt for 16 h before water and EtOAc were added. The organic layer was separated and re-washed twice before it was collected, dried over Na2SO4, and concentrated to provide methyl 3-((2-cyanoethyl)carbamoyl)benzoate as a glassy solid (900 mg). MS found: (M+H)+=233.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washre-washed twice before it
  4. customwas collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0473fe05f81a41509f0a9c65cb25b4d4
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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