HCID 117601879, compound → HCID 117601937, compound

HRID 1773749Notes

Reaction equation

HRID 1773749 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][C:6]1[C:10]([C:11]2[CH:12]=[C:13]([C:23]([OH:32])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:24]=[O:25])[C:14]3[N:18]=[C:17]([O:19]CC)[NH:16][C:15]=3[CH:22]=2)=[C:9]([CH3:33])[O:8][N:7]=1>CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O>[OH:32][C:23]([C:13]1[C:14]2[NH:18][C:17](=[O:19])[NH:16][C:15]=2[CH:22]=[C:11]([C:10]2[C:6]([CH3:5])=[N:7][O:8][C:9]=2[CH3:33])[CH:12]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH:24]([OH:25])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 117601879HCID 117601879, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 117601937HCID 117601937, compound

Reagents, catalysts & solvents 1

HCID 178479889HCID 178479889, compoundSolvent

Procedure

Ethyl magnesiumbromide (3M, 0.61 mL, 1.84 mmol) was added to a solution of 2-(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)-2-hydroxy-2-(pyridin-2-yl)acetaldehyde (120 mg, 0.31 mmol) in methyl-THF at 0° C. After 15 min, the reaction mixture was quenched with 1M HCl, concentrated and a portion of this material was purified by reverse-phase HPLC to give the major diastereomer 4-(1,2-dihydroxy-1-(pyridin-2-yl)butyl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

  1. customthe reaction mixture was quenched with 1M HCl
  2. concentrationconcentrated
  3. customa portion of this material was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-f1ab22f427804ea3af77f18f53291348
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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