Lithium Hydroxide → HCID 56960686, compound

HRID 539233Notes

Reaction equation

HRID 539233 reaction equation
[Cl:1][C:2]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:12]=[C:13]([C:14]([O:16]C)=[O:15])[C:8]=2[N:7]=[C:6]1[CH:24]([F:26])[F:25].[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=2[N:7]=[C:6]1[CH:24]([F:25])[F:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66976997methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate

Product 1

HCID 56960686HCID 56960686, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate (1350 mg, 2.88 mmol) and 2 N LiOH (10 mL) in THF (20 mL) was stirred at 45° C. for 4 h. It was filtered, the filter cake was dissolved in water (10 mL) and formic acid was added to adjust pH=3-4. Then a filtration was performed and the filter cake was dried under vacuum to give the desired product (600 mg, 46%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 3.15 (s, 4H), 3.73 (s, 4H), 5.76 (s, 2H), 6.22 (d, 1H, J=7.5 Hz), 7.20-7.60 (m, 5H), 12.98 (br s, 1H); LC-MS: m/e=456 [M+1]+

Workup

  1. filtrationIt was filtered
  2. dissolutionthe filter cake was dissolved in water (10 mL)
  3. additionformic acid was added
  4. filtrationThen a filtration
  5. customthe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-66eed1e0004a4543958bc69159d1f17f
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Reaction notes

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