2-Chlorobenzylamine → HCID 59738291, compound

HRID 559516Notes

Reaction equation

HRID 559516 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]([OH:10])=O)[CH2:7][CH2:6]1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH2:38][NH2:39]>CN(C=O)C>[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[CH2:38][NH:39][C:8]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:6]1)=[O:10]

Participants

5

Reactant 3

HCID 666482-ChlorobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 138618231-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 59738291HCID 59738291, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(methoxycarbonyl)cyclopropanecarboxylic acid (500 mg, 3.5 mmol) in DMF (5 mL) were added HATU (1.98 g, 5.2 mmol, 1.5 equiv.) and 2-chlorobenzylamine (622 μL, 5.2 mmol, 1.5 equiv.). The reaction mixture was stirred for 2 h. The reaction mixture was purified twice on RP-HPLC using a mixture of acetonitrile and H2O to give methyl 1-(2-chlorobenzylcarbamoyl)cyclopropanecarboxylate (330 mg, 34%). LRMS (M+H+) m/z 268.0.

Workup

  1. customThe reaction mixture was purified twice on RP-HPLC
  2. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-e2ddd9e46c414453a6a6fdf74d39b444
Source dataset
uspto-grants-2011_11
Patent number
US08063082B2

Reaction notes

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