Isoamylamine → HCID 178426807, compound

HRID 2174060Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH3:34])[C:6]([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:7]2[C:11]=1[N:10](S(C1C=CC(C)=CC=1)(=O)=O)[CH:9]=[CH:8]2.[OH-].[K+].C(N)CC(C)C>CCO>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH3:34])[C:6]([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:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-((7-(hydroxymethyl)-5-methyl-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (13 mg, 0.028 mmol), KOH (15.5 mg, 0.276 mmol) and isoamylamine (64 μL, 0.553 mmol) in EtOH (0.8 mL) was stirred at 100° C. using microwave irradiation for 45 minutes. The mixture was directly purified using RP-HPLC (HC-A) to provide the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 10.84 (s, 1H) 7.96 (s, 1H) 7.59 (d, J=8.34 Hz, 1H) 7.45-7.55 (m, 1H) 7.22 (t, J=2.78 Hz, 1H) 6.95 (s, 1H) 6.44-6.51 (m, 1H) 4.74 (s, 2H) 4.47 (s, 2H) 2.39 (s, 3H). HRMS calcd. for C19H16N4O (M+H)+ 317.1402. found 317.1404.

Workup

custommicrowave irradiation for 45 minutes
customThe mixture was directly purified

Sources & evidence

ORD record: ord-f40c0c06314f45f9ba12e58c09c0c3df
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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