Sodium Hydroxide → HCID 66965967, compound

HRID 1514887Notes

Reaction equation

HRID 1514887 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[C:18]([C:20]4[C:30]([CH3:31])=[CH:29][C:23]([O:24][CH2:25][C:26](O)=[O:27])=[CH:22][C:21]=4[CH3:32])[NH:17][C:16]=3[CH:33]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[C:18]([C:20]4[C:21]([CH3:32])=[CH:22][C:23]([O:24][CH2:25][C:26]([N:38]5[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]5)=[O:27])=[CH:29][C:30]=4[CH3:31])[NH:17][C:16]=3[CH:33]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66965700HCID 66965700, compound

Product 1

HCID 66965967HCID 66965967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of {4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenoxy}-acetic acid (53.2 mg), 1-methylpiperazine (12 mg), BOP (62 mg) and DIEA (0.031 mL) in DMF (0.5 mL) was stirred at room temperature for 16 h. Then 1N NaOH aqueous solution was added. The aqueous layer was extracted with EtOAc, and the organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10) and prep-HPLC to give 2-{2,6-dimethyl-4-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-phenyl}-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide: MS (m/z) 526 (M+1).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10)

Sources & evidence

ORD record
ord-01c8fb1201e744958823b260cf0b85a0
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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