Potassium Hydroxide → HCID 178435871, compound

HRID 2174065Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([CH2:28][C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([C:38]#[N:39])=[CH:37][C:31]=3[N:30]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8](S(C1C=CC(C)=CC=1)(=O)=O)[CH:7]=[C:6]2[C:23]1[NH:27][N:26]=[CH:25][CH:24]=1)[CH3:2].[OH-].[K+]>CCO.C(Cl)Cl>[CH2:1]([C:3]1[C:4]([CH2:28][C:29]2[NH:33][C:32]3[CH:34]=[CH:35][C:36]([C:38]#[N:39])=[CH:37][C:31]=3[N:30]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[C:6]2[C:23]1[NH:27][N:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-((5-ethyl-7-methyl-3-(1H-pyrazol-5-yl)-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (63 mg, 0.118 mmol) and KOH (33.1 mg, 0.589 mmol) in EtOH (5 mL) was stirred at 100° C. for 0.5 h under microwave irradiation. The reaction mixture was diluted with CH2Cl2 and filtered through silica gel. The silica gel cake was washed with CH2Cl2/MeOH (c.a. 9/1). After concentration the resulting residue was purified by RP-HPLC (HC-A) to give the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 10.13 (br. s., 1H), 8.53 (s, 1H), 8.23 (d, J=8.60 Hz, 1H), 8.18 (br. d, J=8.60 Hz, 1H), 8.05 (s, 1H), 7.96 (d, J=2.78 Hz, 1H), 7.54 (s, 1H), 6.72 (br. s., 1H), 5.32 (br. s., 2H), 3.38 (q, J=7.60 Hz, 2H), 3.06 (s, 3H), 1.69 (t, J=7.58 Hz, 3H). HRMS calcd. for C23H20N6 (M+H)+ 381.1828. found 381.1828.

Workup

filtrationfiltered through silica gel
washThe silica gel cake was washed with CH2Cl2/MeOH (c.a. 9/1)
concentrationAfter concentration the resulting residue
customwas purified by RP-HPLC (HC-A)

Sources & evidence

ORD record: ord-0237a8d79377417c8514068edb6d520d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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