Potassium Hydroxide → HCID 178435870, compound

HRID 2174067Notes

Reaction equation

HRID 2174067 reaction equation
[CH2:1]([C:3]1[C:4]([CH:29]([OH:41])[C:30]2[NH:34][C:33]3[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:32]=3[N:31]=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[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2].[OH-].[K+]>C(Cl)Cl>[CH2:1]([C:3]1[C:4]([CH:29]([OH:41])[C:30]2[NH:34][C:33]3[CH:35]=[CH:36][C:37]([C:39]#[N:40])=[CH:38][C:32]=3[N:31]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[C:6]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178435673HCID 178435673, compound

Product 1

HCID 178435870HCID 178435870, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (±)-2-((5-ethyl-7-methyl-3-phenyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile (20 mg, 0.036 mmol) and KOH (10 mg, 0.178 mmol) was stirred at 100° C. for 0.5 h under microwave irradiation. The reaction mixture was diluted with CH2Cl2. The mixture was filtered through silica gel. The silica gel cake was washed with CH2Cl2/MeOH (c.a. 9/1). After concentration, the filtrate was purified by silica gel flash column chromatography [CH2Cl2/(5% 2,2,2-trifluoroethanol in CH2Cl2)=95/5 to 40/60] to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 9.54 (br. s., 1H), 7.93 (s, 1H), 7.70 (dd, J=1.30, 8.60 Hz, 1H), 7.63 (d, J=8.60 Hz, 1H), 7.03-7.38 (m, 6H), 6.99 (s, 1H), 6.59 (s, 1H), 2.53-2.54 (m, 5H), 0.98 (t, J=7.33 Hz, 3H). HRMS calcd. for C26H22N4O (M+H)+ 407.1872. found 407.1868.

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. washThe silica gel cake was washed with CH2Cl2/MeOH (c.a. 9/1)
  3. concentrationAfter concentration
  4. customthe filtrate was purified by silica gel flash column chromatography [CH2Cl2/(5% 2,2,2-trifluoroethanol in CH2Cl2)=95/5 to 40/60]

Sources & evidence

ORD record
ord-9ec913288a5b4a03bcc4a8097cabe20d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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