Sodium Hydroxide → HCID 59267697, compound

HRID 1945289Notes

Reaction equation

HRID 1945289 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([OH:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=3)[C:18]([O:20]C)=[O:19])[NH:9][C:8]=2[CH:24]=1>CO.CCOCC>[Cl:3][C:4]1[C:5]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([OH:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]([CH:22]=3)[C:18]([OH:20])=[O:19])[NH:9][C:8]=2[CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 68488240HCID 68488240, compound

Product 1

HCID 59267697HCID 59267697, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2.5 M NaOH (0.2 mL, 0.500 mmol) was added to a solution of methyl 5-({6-chloro-5-[4-(1-hydroxyethyl)phenyl]-1H-benzimidazol-2-yl}oxy)-2-methylbenzoate in MeOH (2.5 mL). Additional 2.5 M NaOH (0.250 mL, 0.625 mmol) was added and the reaction was stirred at rt overnight. The reaction mixture was diluted with Et2O (50 mL) and washed with 10 mL of 1 M aqueous HCl. The aqueous phase was extracted with Et2O. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to afford the desired product. LC-MS: calculated for C23H19ClN2O4 422.86, observed m/e 423.8 (M+H)+ (Rt: 1.74 min). 1H NMR (500 MHz, CD3OD): δ 7.85 (d, 1H), 7.47 (s, 1H), 7.44-7.36 (m, 6H), 7.30 (s, 1H), 4.87 (m, 1H), 2.61 (s, 3H), 1.48 (d, 3H).

Workup

  1. washwashed with 10 mL of 1 M aqueous HCl
  2. extractionThe aqueous phase was extracted with Et2O
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d2a5c65541a4ba4acc96f259190e3b1
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

Loading…