Hydrochloric Acid → HCID 59497234, compound

HRID 1747470Notes

Reaction equation

HRID 1747470 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([O:27][C:28]([F:31])([F:30])[F:29])[CH:21]=2)[C:11]1=[O:32])[CH2:7][CH2:8][CH3:9])C.[OH-].[Li+].Cl>O1CCOCC1.O>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:33])=[O:3])[C:11]2=[O:32])=[CH:21][C:22]=1[O:27][C:28]([F:30])([F:31])[F:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67377783HCID 67377783, compound

Product 1

HCID 59497234HCID 59497234, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3-[3-(4-Amino-3-tri fluoromethoxy-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester—20 mg (0.04 mmol) is dissolved in 1.5 mL of dioxane/water (1:1) and then lithium hydroxide (4.1 mg, 0.17 mmol) is added. The reaction is stirred at room temperature and monitord by LC/MS. Upon completion the reaction is acidified by the addition of 1N HCl. The solvent is evaporated and the residue partitioned between ethyl acetate (2 mL) and water (2 mL). The organic layer is dried over anhydrous sodium sulfate. The solvent is evaporated and the resulting solid is purified by Combi flash chromatography, eluting with 0-20% methanol/dichloromethane to give the title compound (18 mg, 0.04 mmol 95%). LCMS (ESMS): m/z 438.4 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethyl acetate (2 mL) and water (2 mL)
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. customThe solvent is evaporated
  5. customthe resulting solid is purified by Combi flash chromatography
  6. washeluting with 0-20% methanol/dichloromethane

Sources & evidence

ORD record
ord-863a9871c52b4c5984b1ded1b37dbcf3
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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