Cyclopropylamine → HCID 28713267, compound

HRID 1487138Notes

Reaction equation

HRID 1487138 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.C([N:15]([CH:19]([CH3:21])[CH3:20])C(C)C)C.C1(N)CC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([NH:15][CH:19]2[CH2:21][CH2:20]2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27354063-(3-Aminophenyl)propionic 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 28713267HCID 28713267, compoundYield 40.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-(3-aminophenyl)propanoic acid (1 g, 6.05 mmol) in 10 ml DMF, N-ethyl-N-isopropylpropan-2-amine (1.174 g, 9.08 mmol), cyclopropanamine (0.415 g, 7.26 mmol) were added, resulting clear solution was stirred at room temperature, HATU (3.45 g, 9.08 mmol) was added and the resulting mixture was stirred for 24 h at room temperature. Reaction Mixture was diluted with cold water and extraction with Ethyl Acetate (3×30 ml). The Combined organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the crude compound, the crude compound was purified by column chromatography to afford the pure title compound (500 mg).

Workup

  1. customresulting clear solution
  2. stirringthe resulting mixture was stirred for 24 h at room temperature
  3. customReaction Mixture
  4. dry with materialThe Combined organic layer was dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customto give the crude compound
  7. customthe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-cb36c259a5ec449e8c92eac7860078dd
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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