Tetrahydrofuran → HCID 10401042, compound

HRID 1784959Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([C:11](Cl)(Cl)Cl)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[CH3:16].C1C[O:26]CC1>>[CH2:15]([N:17]1[CH2:22][CH2:21][N:20]([C:11]([C:8]2[NH:7][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:10]=3[N:9]=2)=[O:26])[CH2:19][CH2:18]1)[CH3:16]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 791961-Ethylpiperazine

HCID 115578654-Methyl-2-(trichloromethyl)-1H-benzimidazole

Product 1

HCID 10401042HCID 10401042, compoundYield 62%

Procedure

The reaction was carried out as described in General Procedure 2 using 4-methyl-2-trichloromethyl-1H-benzoimidazole (Example 20, Step A, 100 mg, 0.40 mmol) and N-ethylpiperazine (0.10 mL, 0.80 mmol) in THF (3 mL). Purification afforded 67 mg (62%) of the title compound. MS (ESI): mass calculated for C15H20N4O, 272.16; m/z found, 273.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 10.89 (s, 1H), 7.64 (d, J=8.6 Hz, 0.5H), 7.33 (d, J=8.6 Hz, 0.5H), 7.22-7.18 (m, 1H), 7.13 (d, J=7.4 Hz, 0.5H), 7.10 (d, J=7.4 Hz, 0.5H), 4.86-4.84 (m, 1H), 4.80-4.78 (m, 1H), 3.93-3.90 (m, 2H), 2.66 (s, 1.5H), 2.63-2.56 (m, 4H), 2.52 (s, 1.5H), 2.48 (q, J=7.3 Hz, 2H), 1.14 (t, J=7.1 Hz, 3H).

Workup

customPurification

Sources & evidence

ORD record: ord-8e3a28d790714c6995672309acff838e
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504426B2

Reaction notes

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