Sodium Hydroxide → HCID 45256866, compound

HRID 1945291Notes

Reaction equation

HRID 1945291 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:5]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)=[CH:6][C:7]2[N:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20]([O:22]C)=[O:21])[CH:14]=3)[NH:9][C:8]=2[CH:24]=1>CO.O>[C:20]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[CH3:19])[O:12][C:10]1[NH:9][C:8]2[CH:24]=[C:4]([F:3])[C:5]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][CH:32]=4)=[CH:27][CH:26]=3)=[CH:6][C:7]=2[N:11]=1)([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86640505HCID 86640505, compound

Product 1

HCID 45256866HCID 45256866, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5 M aqueous NaOH (3 mL) was added to a solution of ethyl, 4′-{6-fluoro-2-[3-(methoxycarbonyl)-4-methylphenoxy]-1H-benzimidazol-5-yl}biphenyl-4-carboxylate (750 mg, 1.43 mmol) in MeOH (30 mL). The solution was diluted with water until cloudy and heated at 70° C. for 20 min. Volatiles were removed and the residue was-dissolved in 20 ml water and acidified with 2 N aqueous HCl. The precipitated white solid was filtered and dried to afford the title compound as a white solid. LC-MS: calculated for C28H19FN2O5 482.46, observed m/e 483.11 (M+H)+ (Rt 1.91/4.0 min). 1H NMR (500 MHz, CD3OD): δ 8.18-7.25 (m, 13H), 2.62 (s, 3H).

Workup

  1. customVolatiles were removed
  2. dissolutionthe residue was-dissolved in 20 ml water
  3. filtrationThe precipitated white solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-badac8c34f314759b1c15560a0394698
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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