Isoamylamine → HCID 178489056, compound

HRID 2174072Notes

Reaction equation

HRID 2174072 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:23]([C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([C:35]#[N:36])=[CH:34][C:28]=3[N:27]=2)([CH3:25])[CH3:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8](S(C1C=CC(C)=CC=1)(=O)=O)[CH:7]=[CH:6]2.[OH-].[K+].C(N)CC(C)C>CCO>[CH3:1][O:2][C:3]1[C:4]([C:23]([C:26]2[NH:30][C:29]3[CH:31]=[CH:32][C:33]([C:35]#[N:36])=[CH:34][C:28]=3[N:27]=2)([CH3:25])[CH3:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 14797Potassium HydroxideHCID 178488598HCID 178488598, compound

Product 1

HCID 178489056HCID 178489056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-(5-methoxy-7-methyl-1-tosyl-1H-indol-4-yl)propan-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (43 mg, 0.086 mmol) and KOH (48.4 mg, 0.862 mmol) and isoamylamine (150 μL, 1.29 mmol) in EtOH (1.2 mL) was heated at 100° C. under microwave irradiation for 2 h. The reaction mixture was loaded onto silica gel and was purified by silica gel flash chromatography (0-50% EtOAc:DCM), and then SFC using a 2-ethylpyridine column with 12% MeOH+0.2% DEA in CO2. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.19 (s, 1H) 10.88 (br. s., 1H) 8.08 (m) 7.66-7.76 (m) 7.37-7.53 (m) 7.04-7.18 (m, 1H) 6.73 (s, 1H) 5.89 (m) 5.83 (m) 3.45 (m) 3.43 (m) 2.43 (s, 3H) 1.90 (s, 6H). HRMS calcd. for C21H20N4O (M+H)+ 345.1715. found 345.1724.

Workup

  1. customwas purified by silica gel flash chromatography (0-50% EtOAc:DCM)

Sources & evidence

ORD record
ord-d0630c0151f24350a26219b33bcb33ef
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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