Lithium Hydroxide → HCID 56960687, compound

HRID 44555Notes

Reaction equation

HRID 44555 reaction equation
Cl[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-].[CH2:34]1COCC1>>[Cl:31][C:30]1[C:2]([CH3:34])=[C:3]([CH2:4][N:5]2[C:9]3[CH:10]=[C:11]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=3[N:7]=[C:6]2[CH:24]([F:26])[F:25])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66976997methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate

Product 1

HCID 56960687HCID 56960687, compoundYield 80%

Conditions

Temperature
45 °C

Procedure

A solution of methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate (1045 mg, 2.3 mmol) in THF (40 mL) was added into 2 N LiOH (20 mL) and the mixture was stirred at 45° C. for 4 h. It was filtered, the filter cake was added to water (100 mL) and formic acid was added to adjust pH=3. Then a filtration was performed, the filter cake was collected and washed with water (200 mL), dried under vacuum to give the desired product (800 mg, 80%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.46 (s, 3H), 3.13 (t, 4H, J=4.8 Hz), 3.73 (t, 4H, J=4.8 Hz), 3.92 (s, 3H), 5.70 (s, 2H), 6.00 (d, 1H, J=7.5 Hz), 7.04 (t, 1H, J=7.5 Hz), 7.23 (d, 1H, J=1.8 Hz), 7.34 (t, 1H, J=7.5 Hz), 7.36 (t, 1H, J=51.9 Hz), 7.57 (d, 1H, J=1.8 Hz), 12.96 (br s, 1H); LC-MS: m/e=436 [M+1]+

Workup

  1. filtrationIt was filtered
  2. additionthe filter cake was added to water (100 mL) and formic acid
  3. additionwas added
  4. filtrationThen a filtration
  5. customthe filter cake was collected
  6. washwashed with water (200 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4513df678eb342a3a3d5f8abd116429e
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Reaction notes

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