1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68832536, compound

HRID 1787927Notes

Reaction equation

HRID 1787927 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18](O)=[O:19])=[O:10])=[C:7]([O:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]2[O:10][C:18](=[O:19])[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[C:7]([O:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:26][CH2:25]2)[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68833121HCID 68833121, compound

Product 1

HCID 68832536HCID 68832536, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]pyridine-3-carboxylic acid (0.15 g, 0.30 mmol) in DMF (5 mL) was added 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride (0.077 g, 0.39 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed twice with ice water/brine. The combined aq phase was back extracted with ethyl acetate and the combined organic phase was dried with MgSO4, filtered and concentrated in vacuo to give the title compound (0.121 g, 84%) as a light yellow foam.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed twice with ice water/brine
  4. extractionThe combined aq phase was back extracted with ethyl acetate
  5. dry with materialthe combined organic phase was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f4dfec2d1b249969514a1e3303875f6
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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