Pyridine → HCID 67166415, compound

HRID 553253Notes

Reaction equation

HRID 553253 reaction equation
Cl.C(N=C=N[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])C)C.[OH2:13].ON1[C:19]2[CH:20]=C[CH:22]=[CH:23][C:18]=2N=N1.C(C1C=CC2N=C([C:39]3[O:43][C:42]([C:44](O)=[O:45])=[CH:41][CH:40]=3)NC=2C=1)(=O)C1C=CC=CC=1.[NH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1.[N:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[C:56]([C:57]1[CH:7]=[CH:8][C:9]2[N:10]=[C:12]([C:40]3[CH:41]=[C:42]([C:44]([N:49]4[CH2:53][CH2:52][CH2:51][CH2:50]4)=[O:45])[O:43][CH:39]=3)[NH:54][C:59]=2[CH:58]=1)(=[O:13])[C:55]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 579557865-(6-Benzoyl-1H-benzimidazol-2-yl)furan-2-carboxylic acid

Product 1

HCID 67166415HCID 67166415, compoundYield 88%

Conditions

Temperature
70 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (63 mg, 0.33 mmol) and 1-hydroxybenzotriazole monohydrate (51 mg, 0.33 mmol) were added to a pyridine (4 ml) solution of the 5-(5-benzoylbenzimidazol-2-yl)-furan-2-carboxylic acid (100 mg, 0.30 mmol) obtained in Example 57. Pyrrolidine (21 mg, 0.30 mmol) was added and then heated. The reaction mixture was stirred at 70° C. for 6 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 (4-(5-benzoylbenzimidazol-2-yl)-2-furanylcarbonyl)pyrrolidine (102 mg, 88%) as a brown oil.

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-6a49c8eee2cc4ce2a53b8489e9a1be9f
Source dataset
uspto-grants-2011_05
Patent number
US07951956B2

Reaction notes

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