Cyclopropylamine → 5-Hydroxymethyl-pyridine-2-carboxylic acid cyclopropylamide

HRID 851969Notes

Reaction equation

HRID 851969 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1.[B-](F)(F)(F)F.CN(C(O[N:25]1[C:30](=O)[CH:29]=[CH:28]C=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[CH:30]1([NH:25][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:8][N:7]=2)=[O:11])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 135185635-(Hydroxymethyl)pyridine-2-carboxylic acid

Product 1

HCID 694914535-Hydroxymethyl-pyridine-2-carboxylic acid cyclopropylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Hydroxymethyl-pyridine-2-carboxylic acid (0.23 g, 1.5 mmol) was dissolved in DMF (3 ml) and activated with TPTU (0.45 g, 1.5 mmol), Hünig's base (0.51 ml, 3.0 mmol) and reacted with cyclopropyl amine (0.12 ml, 1.65 mmol) for 1 h at r.t during which a precipitate was formed. Solvent was removed and the residue dissolved in acetonitrile/water and purified by prep.RP(C18)HPLC: 60 mg;

Workup

  1. customwas formed
  2. customSolvent was removed
  3. dissolutionthe residue dissolved in acetonitrile/water
  4. custompurified by prep.RP(C18)HPLC: 60 mg

Sources & evidence

ORD record
ord-ecb1f1d616ea4181beade1ca658b9927
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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