Potassium Hydroxide → HCID 178489058, compound

HRID 2174132Notes

Reaction equation

HRID 2174132 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8]([C:10]([C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)([CH3:17])[CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].[OH-].[K+]>CO>[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8]([C:10]([C:18]3[C:26]([O:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)([CH3:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178500186HCID 178500186, compound

Product 1

HCID 178489058HCID 178489058, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-Methyl 4-(5-cyano-1H-benzo[d]imidazol-2-yl)-4-(5-methoxy-7-methyl-1H-indol-4-yl)pentanoate (Example 155-L) (8.5 mg, 0.020 mmol) was dissolved in MeOH (300 μL) and then treated with 10% aq. KOH (70 μl, 0.125 mmol) and stirred at room temperature for 30 minutes. The reaction was directly purified using preparative HPLC (HC-B) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.87 (br. s., 1H) 7.92 (br. s.) 7.53 (br. s.) 7.42-7.49 (m) 7.09 (t, J=2.78 Hz, 1H) 6.73 (s, 1H) 5.62 (br. s., 1H) 3.43 (s, 3H) 2.55-2.64 (m, 2H) 2.42 (s, 3H) 1.95-2.05 (m, 2H) 1.88 (s, 3H). MS (ESI+) m/z 403.3 (M+H).

Workup

  1. customThe reaction was directly purified

Sources & evidence

ORD record
ord-8791696daa9248a990e3741f7d5ed1d9
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…