Tetrahydrofuran → HCID 69064692, compound

HRID 2111785Notes

Reaction equation

HRID 2111785 reaction equation
C1COCC1.[F:6][C:7]([F:37])([F:36])[O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C:25]4[CH:26]=[CH:27][C:28]([C:30]([O:32]C)=[O:31])=[CH:29][C:24]=4[N:23]=[CH:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[OH-].[Na+]>CO>[F:37][C:7]([F:6])([F:36])[O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]3[C:25]4[CH:26]=[CH:27][C:28]([C:30]([OH:32])=[O:31])=[CH:29][C:24]=4[N:23]=[CH:22]3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69068939HCID 69068939, compound

Product 1

HCID 69064692HCID 69064692, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 0.5M THF solution of methyl 1-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxylate (3.7 g, 8.4 mmol) was treated with 10M NaOH (8.4 mL, 84 mmol) and enough methanol to make the mixture homogeneous. The reaction mixture was then heated at 70° C. for 24 h, after which it was concentrated in vacuo, taken up in water and acidified to pH 4 with 2M HCl(aq). The resulting precipitate was filtered and washed with water to afford 1-(4-{[4-(trifluoromethoxy) benzyl]oxy}phenyl)-1H-benzimidazole-5-carboxylic acid. 1H NMR (DMSO-d6, 400 MHz) δ 5.26 (s, 2H), 7.26-7.29 (m, 2H), 7.43 (d, 2H, J=8.0 Hz), 7.58 (d, 1H, J=8.0 Hz), 7.63-7.66 (m, 4H), 7.94 (dd, 1H, J=8.8 Hz, 1.6 Hz), 8.33 (d, 1H, J=0.8 Hz), 8.62 (s, 1H); MS (ES+): m/z 429 (MH+).

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-672b9bd670614ea296d6287788e49515
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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