Water → HCID 86722596, compound

HRID 1503071Notes

Reaction equation

HRID 1503071 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:20][NH:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].O>CN(C1C=CN=CC=1)C.ClCCCl>[CH:1]1([C:4]([N:21]([CH3:20])[NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 15655Cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24801390N'-methyl(benzyloxy)carbohydrazide hydrochloride

Product 1

HCID 86722596HCID 86722596, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

Cyclopropanecarboxylic acid (600 mg, 6.97 mmol), DMAP (170 mg, 1.39 mmol) and EDC.HCl (1.19 g, 7.67 mmol) were added in that order to a stirred solution of benzyl 2-methylhydrazinecarboxylate hydrochloride (JOC, 2013, 78, 3541-3552.) (1.80 g, 8.37 mmol) in DCE (10 mL) and the reaction mixture was stirred at 25° C. for 12 h. Water was added to the reaction mixture and the mixture extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% hexane in EtOAc to afford the title compound as a colourless gum (1.6 g, 80%): 1H NMR (300 MHz, DMSO-d6) δ10.01 (bs, 1H), 7.37 (s, 5H), 5.18 (s, 2H), 2.97 (s, 3H), 1.98-1.89 (m, 1H), 0.70-0.68 (m, 4H); ESIMS m/z 247.0 ([M−H]−); IR (thin film) 3502, 2928, 1736 cm−1.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography on silica (100-200 mesh)
  7. washeluting with 30% hexane in EtOAc

Sources & evidence

ORD record
ord-fb45681afd3d498c8da078dd9d50a7bf
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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