Hydrochloric Acid → HCID 178524455, compound

HRID 1842504Notes

Reaction equation

HRID 1842504 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7](C)=[N:6][C:5]=1[N:11]1[CH2:14][CH:13]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=3[N:16]=2)[CH2:12]1.O.[Li+].[OH-].Cl>CO>[Cl:24][C:22]1[CH:21]=[CH:20][C:18]2[NH:19][C:15]([CH:13]3[CH2:12][N:11]([C:5]4[N:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:25])=[O:2])[CH2:14]3)=[N:16][C:17]=2[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 178497912HCID 178497912, compound

Product 1

HCID 178524455HCID 178524455, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-[3-(5-chloro-1H-benzoimidazol-2-yl)-azetidin-1-yl]-nicotinic acid methyl ester (1.6 g, 4.6 mmol) and water (10 mL) in MeOH (10 mL) at RT was treated with LiOH (414 mg, 9.87 mmol). The mixture was stirred at RT overnight, and made acidic with a 10% HCl solution. The resulting solution was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was triturated with hexanes and washed several times with hexanes to give the desired carboxylic acid as a white crystalline solid (1.1 g, yield 71%).

Workup

  1. extractionThe resulting solution was extracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexanes
  6. washwashed several times with hexanes

Sources & evidence

ORD record
ord-a0650e707a7843b6b8a91d12abcbcf87
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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