Isoamylamine → HCID 178424035, compound

HRID 2174039Notes

Reaction equation

HRID 2174039 reaction equation
[CH3:1][C:2]1[C:3]([CH:22]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([C:34]#[N:35])=[CH:33][C:27]=3[N:26]=2)[CH2:23][OH:24])=[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.C(N)CC(C)C.[OH-].[K+]>CCO>[CH3:1][C:2]1[C:3]([CH:22]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([C:34]#[N:35])=[CH:33][C:27]=3[N:26]=2)[CH2:23][OH:24])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 14797Potassium HydroxideHCID 178427336HCID 178427336, compound

Product 1

HCID 178424035HCID 178424035, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (±)-2-(1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)-2-hydroxyethyl)-1H-benzo[d]imidazole-5-carbonitrile, isoamylamine (103 mg, 1.18 mmol) and KOH (66.0 mg, 1.18 mmol) in EtOH (2 mL) was stirred at 100° C. for 30 min under microwave irradiation. The reaction mixture was concentrated and the residue was partitioned between EtOAc and sat. aq. NH4Cl. The aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried over sodium sulfate and concentrated. The residue was purified with reverse phase HPLC (HC-B) to provide the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) 9.18 (br. s., 1H) 7.87 (br. s., 1H) 7.47 (d, J=7.07 Hz, 2H) 7.01 (t, J=2.84 Hz, 1H) 6.85 (s, 1H) 5.79-5.86 (m, 1H) 4.92 (dd, J=8.91, 5.49 Hz, 1H) 4.59 (dd, J=10.99, 9.09 Hz, 1H) 3.92 (dd, J=11.05, 5.49 Hz, 1H) 2.42 (s, 6H). MS (ESI+) m/z 331.3 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and sat. aq. NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with reverse phase HPLC (HC-B)

Sources & evidence

ORD record
ord-b5e2c3ebf3f44b7a88315d8d008477d8
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…