Hydrochloric Acid → HCID 59497416, compound

HRID 1747430Notes

Reaction equation

HRID 1747430 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH3:29])[N:22]([CH3:30])[CH:21]=2)[C:11]1=[O:31].Cl>O1CCOCC1.O>[CH3:30][N:22]1[C:23]2[C:28](=[C:27]([CH3:29])[CH:26]=[CH:25][CH:24]=2)[C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:32])=[O:2])[C:11]2=[O:31])=[CH:21]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59497288HCID 59497288, compound

Product 1

HCID 59497416HCID 59497416, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-benzoic acid methyl ester (45 mg, 0.11 mmol) in 1,4-dioxane (1.0 mL) is added LiOH monohydrate (5.6 mg, 0.13 mmol) in water (0.1 mL) at room temperature. The solution is stirred at the same temperature for 16 hours. Then another 1.0 mg of LiOH monohydrate is added and the reaction is continued for another 2 hr. Then 0.5 mL of 1.0 M HCl is added along with 10 mL of water. The mixture is extracted with EtOAc (3×15 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by preparative TLC affords 41 mg (95%) of 2-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-benzoic acid. LCMS (ESMS): m/z 412.17 (M+H+).

Workup

  1. waitthe reaction is continued for another 2 hr
  2. extractionThe mixture is extracted with EtOAc (3×15 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by preparative TLC

Sources & evidence

ORD record
ord-fd5b6f181aaf422498e18aa8d78731b1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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