Isoamylamine → HCID 178424030, compound

HRID 2173988Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH2:22][C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[CH:5]2.[OH-].[K+].C(N)CC(C)C>CCO.C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:22][C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:25]=3[N:24]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-((5,7-dimethyl-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (370 mg, 0.814 mmol), KOH (457 mg, 8.14 mmol), and isoamylamine (1.892 mL, 16.28 mmol) in EtOH (15 mL) was stirred at 100° C. under microwave irradiation for 2 hr. The reaction mixture was diluted with CH2Cl2. The mixture was filtered through SiO2 pad. The SiO2 cake was washed with a mixture of CH2Cl2/MeOH (c.a. 6/1). The organic solution was concentrated and purified by silica gel flash column chromatography [(5% 2,2,2-trifluoroethanol in CH2Cl2)/MeOH=1/0 to 85/15] to give the title compound. 1H NMR (400 MHz, DMSO-d6, with about 5 μL TFA) δ ppm 11.01 (br. s., 1H), 8.05 (s, 1H), 7.67 (br. d, J=8.30 Hz, 1H), 7.62 (br. d, J=8.30 Hz, 1H), 7.26 (t, J=2.80 Hz, 1H), 6.79 (s, 1H), 6.43 (dd, J=1.80, 2.80 Hz, 1H), 4.53 (s, 2H), 2.43 (s, 3H), 2.35 (s, 3H). HRMS calcd. for C19H16N4 (M+H)+ 301.1448. found 301.1459.

Workup

filtrationThe mixture was filtered through SiO2 pad
washThe SiO2 cake was washed with a mixture of CH2Cl2/MeOH (c.a. 6/1)
concentrationThe organic solution was concentrated
custompurified by silica gel flash column chromatography [(5% 2,2,2-trifluoroethanol in CH2Cl2)/MeOH=1/0 to 85/15]

Sources & evidence

ORD record: ord-3875c28b85f84baa94233fd75b9d3acc
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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