Hydrochloric Acid → HCID 10195437, compound

HRID 2416920Notes

Reaction equation

HRID 2416920 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17](=[O:26])[N:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[CH:16][C:11]=2[N:10]=[C:9]1[NH:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:29])C.[OH-].[Na+].Cl>CO.O.C(Cl)Cl>[CH:20]1([N:18]([CH3:19])[C:17]([C:15]2[CH:14]=[CH:13][C:12]3[N:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:35])=[O:3])[C:9]([NH:27][C:28]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)=[O:29])=[N:10][C:11]=3[CH:16]=2)=[O:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10228566HCID 10228566, compound

Product 1

HCID 10195437HCID 10195437, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-{5-(N-cyclohexyl-N-methyl-carbamoyl)-2-[(thiophene-2-carbonyl)-amino]-benzoimidazol-1-yl}-butyric acid ethyl ester (Example 1) (0.5 g, 1.0 mmol) in MeOH (10 mL) and water (10 mL) was added solid NaOH (0.12 g, 3 mmol). The reaction was complete in 4 h. The mixture was acidified with 1N HCl, and was diluted with CH2Cl2 (20 mL). The organic layer was dried over magnesium sulfate, the solvent evaporated and the residue purified by flash chromatography with 10% MeOH/dichloromethane to give the title compound (0.43 g, 92%), m.p. 256-258° C.

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. customthe solvent evaporated
  3. customthe residue purified by flash chromatography with 10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-7c23b208c2cc446faf73211162800247
Source dataset
uspto-grants-2004_11
Patent number
US06825219B2

Reaction notes

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