Lithium Hydroxide → HCID 178489054, compound

HRID 2174116Notes

Reaction equation

HRID 2174116 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)[CH:11]([CH3:16])[C:12]([O:14]C)=[O:13])=[N:9][C:5]=2[CH:4]=1)#[N:2].[Li+].[OH-]>CO.O>[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)[CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178500113HCID 178500113, compound

Product 1

HCID 178489054HCID 178489054, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To (±)-methyl 3-(5-cyano-1H-benzo[d]imidazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)-2-methylpropanoate (diastereomer A, Example 147-B) (45 mg, 0.11 mmol) was added LiOH (50 mg, 2.0 mmol) in MeOH/Water (3 mL:0.8 mL) and the reaction was heated at 60° C. overnight. The reaction was concentrated, diluted with ethyl acetate (100 mL) and 1 M HCl (20 mL). The organic layer was removed, dried over sodium sulfate and purified via RP-FCC (ACN/water) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.63-10.91 (m, 1H) 7.97 (br. s., 1H) 7.56 (br. s., 1H) 7.44-7.50 (m, 1H) 7.13-7.18 (m, 1H) 6.74 (s, 1H) 6.26 (br. s., 1H) 5.15 (d, J=9.29 Hz, 1H) 3.82 (s, 3H) 3.61-3.73 (m, 1H) 2.40 (s, 3H) 1.25 (d, J=6.97 Hz, 3H). HRMS calcd. for C22H20N4O3 (M+H)+ 389.1605. found 389.1604.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate (100 mL) and 1 M HCl (20 mL)
  3. customThe organic layer was removed
  4. dry with materialdried over sodium sulfate
  5. custompurified via RP-FCC (ACN/water)

Sources & evidence

ORD record
ord-e823959a8c08494880d6a517952a309b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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