HCID 59267736, compound → HCID 45256690, compound

HRID 1945290Notes

Reaction equation

HRID 1945290 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:29]([Cl:30])=[CH:28][C:13]3[NH:14][C:15]([O:17][C:18]4[CH:19]=[CH:20][C:21]([CH3:27])=[C:22]([CH:26]=4)[C:23]([OH:25])=[O:24])=[N:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:31][Mg+].[Br-]>C1COCC1.CCOCC>[Cl:30][C:29]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:31])[CH3:2])=[CH:9][CH:8]=2)=[CH:11][C:12]2[N:16]=[C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([CH3:27])=[C:22]([CH:26]=3)[C:23]([OH:25])=[O:24])[NH:14][C:13]=2[CH:28]=1

Participants

5

Reactant 2

HCID 59267736HCID 59267736, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 45256690HCID 45256690, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of 5-{[5-(4-acetylphenyl)-6-chloro-1H-benzimidazol-2-yl]oxy}-2-methylbenzoic acid (52 mg, 0.124 mmol) and CeCl3 (244 mg, 0.988 mmol) in THF (4 mL) was added MeMgBr (1.4 M in THF) (0.618 mL, 0.865 mmol) dropwise via syringe. The reaction was stirred at rt for 30 min, diluted with Et2O (50 mL) and washed with 1 M HCl (10 mL). The aqueous phase was extracted with Et2O. The combined organics were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. Purification by reverse phase HPLC eluting with MeCN:H2O afforded the desired product as an off-white solid. LC-MS: calculated for C24H21ClN2O4 436.89, observed m/e 437.2 (M+H)+ (Rt: 1.81 min). 1 H NMR (500 MHz, CD3OD): δ 7.89 (d, 1H), 7.54 (d, 2H), 7.49 (s, 1H), 7.47-7.39 (m, 2H), 7.37 (m, 2H), 7.32 (s, 1H), 2.62 (s, 3H), 1.57 (s, 6H).

Workup

  1. washwashed with 1 M HCl (10 mL)
  2. extractionThe aqueous phase was extracted with Et2O
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase HPLC
  8. washeluting with MeCN

Sources & evidence

ORD record
ord-34942bf0527843cabc26fb07d1609785
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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