Sodium Hydroxide → HCID 178489061, compound

HRID 2174112Notes

Reaction equation

HRID 2174112 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8]([CH:10]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8]([CH:10]([C:17]3[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[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 14798Sodium HydroxideHCID 178500114HCID 178500114, compound

Product 1

HCID 178489061HCID 178489061, 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)butanoate (Example 146-B) (40 mg, 0.099 mmol) was dissolved in MeOH (1 mL) and then added 1 N NaOH (248 μl, 0.248 mmol). The reaction was stirred at room temperature for 3 h, concentrated and then directly purified via RP-HPLC (HC-B) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) d ppm 10.92 (br. s., 1H) 7.61-8.32 (m, 1H) 7.47-7.51 (m, 2H) 7.13 (d, J=5.56 Hz, 1H) 6.79 (s, 1H) 5.99 (br. s., 1H) 4.90 (dd, J=8.59, 5.81 Hz, 1H) 3.74 (s, 3H) 2.72-2.82 (m, 1H) 2.45 (s, 3H) 2.20-2.32 (m, 2H) 2.06-2.18 (m, 1H). HRMS calcd. for C22H20N4O3 (M+H)+ 389.1605. found 389.1604.

Workup

  1. concentrationconcentrated
  2. customdirectly purified via RP-HPLC (HC-B)

Sources & evidence

ORD record
ord-be12c99d1fab4b7ba4ca7ee8b680ea42
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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