Piperazine → HCID 178519934, compound

HRID 1784958Notes

Reaction equation

HRID 1784958 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C1C[O:24]CC1>>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:24])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 8028TetrahydrofuranHCID 178477904HCID 178477904, compound

Product 1

HCID 178519934HCID 178519934, compoundYield 10%

Procedure

The reaction was carried out as described in General Procedure 2 with commercially available 5-chloro-2-trichloromethyl-1H-benzoimidazole (100 mg, 0.37 mmol) and piperazine (64 mg, 0.75 mmol) in THF (3 mL). Purification afforded 10 mg (10%) of the title compound. MS (ESI): mass calculated for C12H13ClN4O, 264.08; m/z found, 265.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.29 (s, 1H), 7.67 (br s, 2H), 7.33 (d, J=8.6 Hz, 2H), 4.50-4.47 (m, 2H), 3.71 (t, J=4.6 Hz, 2H), 2.41-2.39 (m, 4H), 2.22 (s, 3H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-9bf372b83196459a83b8c596b56048fe
Source dataset
uspto-grants-2009_03
Patent number
US07504426B2

Reaction notes

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