N,N-Dimethylethylenediamine → HCID 57955765, compound

HRID 553243Notes

Reaction equation

HRID 553243 reaction equation
Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:24]([C:32]1[CH:58]=[CH:57][C:35]2[N:36]=[C:37]([C:39]3[C:40]([CH3:56])=[C:41]([C:45]([N:47]4[CH2:52][CH2:51][CH:50]([C:53]([OH:55])=O)[CH2:49][CH2:48]4)=[O:46])[NH:42][C:43]=3[CH3:44])[NH:38][C:34]=2[CH:33]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH3:59][N:60]([CH3:64])[CH2:61][CH2:62][NH2:63]>N1C=CC=CC=1>[CH3:59][N:60]([CH2:61][CH2:62][NH:63][C:53]([CH:50]1[CH2:51][CH2:52][N:47]([C:45]([C:41]2[NH:42][C:43]([CH3:44])=[C:39]([C:37]3[NH:38][C:34]4[CH:33]=[C:32]([C:24](=[O:31])[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:58]=[CH:57][C:35]=4[N:36]=3)[C:40]=2[CH3:56])=[O:46])[CH2:48][CH2:49]1)=[O:55])[CH3:64]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57955809HCID 57955809, compound

Product 1

HCID 57955765HCID 57955765, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (31 mg, 0.16 mmol) and 1-hydroxybenzotriazole monohydrate (25 mg, 0.16 mmol) were added to a pyridine (4 ml) solution of the ((4-(5-benzoylbenzimidazol-2-yl)-3,5-dimethylpyrrol-2-yl)-carbonyl)piperidine-4-carboxylic acid (70 mg, 0.15 mmol) obtained in Example 45. N,N-Dimethylethylenediamine (13 mg, 0.15 mmol) was added to the reaction mixture and heated. The reaction mixture was stirred at 60° C. (internal temperature) for 10 hours, and then allowed to cool to room temperature with stirring. The solvent was evaporated, and the residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2) to afford N-dimethylaminoethyl-1-((4-(5-benzoylbenzimidazol-2-yl)-3,5-dimethylpyrrol-2-yl)-carbonyl)piperidine-4-carboxamide (44 mg, 55%) as white crystals.

Workup

  1. temperatureheated
  2. temperatureto cool to room temperature
  3. stirringwith stirring
  4. customThe solvent was evaporated
  5. customthe residue was purified

Sources & evidence

ORD record
ord-45b20e7bd0f8451291a8ac8cfcbf04bd
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

Loading…