Cyclopropylamine → HCID 68740396, compound

HRID 2246789Notes

Reaction equation

HRID 2246789 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:25]=[CH:26][CH:27]=[N:28]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>CN(C)C=O.C(=O)(O)[O-].[Na+].CCOCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([NH:28][CH:27]2[CH2:25][CH2:26]2)=[O:13])=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12586658rac-(1R,2R)-2-(4-bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 68740396HCID 68740396, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylic acid from Step 1 (300 mg, 1.24 mmoles) in dimethylformamide (5 mL) at room temperature was added HATU (500 mg, 1.31 mmoles) followed by cyclopropylamine (0.44 mL, 6.2 mmoles). The reaction mixture was stirred overnight and diluted with half-saturated sodium bicarbonate aqueous solution (50 mL), ether (50 mL) and ethyl acetate (50 mL). The phases were separated and the organic layer was washed with water twice (30 mL each portion), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified onto a short column of silica gel using 50% ethyl acetate diethyl ether to give the title compound.

Workup

  1. customThe phases were separated
  2. washthe organic layer was washed with water twice (30 mL each portion)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified onto a short column of silica gel using 50% ethyl acetate diethyl ether

Sources & evidence

ORD record
ord-d92856f0079a467599587fa51f2d287d
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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