3-Aminopropionitrile → Methyl 3-tert-butyl-5-((2-cyanoethyl)carbamoyl)benzoate

HRID 2225194Notes

Reaction equation

HRID 2225194 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=1)[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][CH2:43][CH2:44][C:45]#[N:46].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[C:1]([C:5]1[CH:13]=[C:12]([CH:11]=[C:7]([C:8](=[O:10])[NH:46][CH2:45][CH2:44][C:43]#[N:42])[CH:6]=1)[C:14]([O:16][CH3:17])=[O:15])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 16473-AminopropionitrileHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 121446585-tert-Butyl-isophthalic acid monomethyl ester

Product 1

HCID 21075155Methyl 3-tert-butyl-5-((2-cyanoethyl)carbamoyl)benzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation H6, Step 2: To a soultion of 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (700 mg) in DMF (15 mL) at rt was added HATU (1.2 eq), 3-aminopropanenitrile (1.2 eq), and iPr2NEt (1.2 eq). 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-tert-butyl-5-((2-cyanoethyl)carbamoyl)benzoate as a glassy solid (520 mg). MS found: (M+H)+=289.

Workup

  1. customPreparation H6, Step 2
  2. additionwere added
  3. customThe organic layer was separated
  4. washre-washed twice before it
  5. customwas collected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e2142cd896f841cd9db9c4f5eaf1d763
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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