Cyclopropylamine → HCID 67094421, compound

HRID 1435502Notes

Reaction equation

HRID 1435502 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.[C:29]([O:33][C:34]([N:36]1[CH2:40][CH2:39][C@H:38]([C:41](O)=[O:42])[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]1([NH:28][C:41]([C@H:38]2[CH2:39][CH2:40][N:36]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[CH2:37]2)=[O:42])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 1512492(3S)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic 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 67094421HCID 67094421, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.97 g, 2.5 mmol) and cyclopropylamine (0.14 g, 2.5 mmol) were added to a solution of (3S)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (0.50 g, 2.3 mmol) and DIPEA (0.48 mL, 2.7 mmol) in DMF (15 mL). The reaction mixture was stirred for 3 h and the solvent was concentrated. The product was recovered in EtOAc and washed with water, saturated NaHCO3 solution, water and brine. The organic layer was dried over anhydrous MgSO4 and the solvent was concentrated to provide tert-butyl (3S)-3-[(cyclopropylamino)carbonyl]pyrrolidine-1-carboxylate as white solid. The intermediate was recovered in TFA (5 mL) and stirred for 2 h. The solvent was concentrated to provide the title compound as yellow oil that was used for the next step without further purification. Yield: 0.21 g (33%).

Workup

  1. concentrationthe solvent was concentrated
  2. customThe product was recovered in EtOAc
  3. washwashed with water, saturated NaHCO3 solution, water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-6913679293d846019efbd4300891aacb
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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