Hydrochloric Acid → HCID 17747132, compound

HRID 2246432Notes

Reaction equation

HRID 2246432 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][N:5]1[C:13]2[CH:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=3)[N:10]=[C:9]([C:27]#[N:28])[C:8]=2[N:7]=[CH:6]1.CN(C)C=O.[OH-].[Li+].Cl>O>[C:27]([C:9]1[C:8]2[N:7]=[CH:6][N:5]([CH2:4][C:3]([OH:29])=[O:2])[C:13]=2[CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[C:16]([C:23]([F:26])([F:25])[F:24])[CH:15]=2)[N:10]=1)#[N:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6228Dimethylformamide2×HCID 58938129HCID 58938129, compound

Product 1

HCID 17747132HCID 17747132, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of [4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-imidazo[4,5-c]-pyridin-1-yl]-acetic acid methyl ester (110 mg, 0.27 mmol) in a 1:1 mixture of dimethylformamide (2 ml) and water (2 ml) was added lithium hydroxide (19 mg, 0.81 mmol) dissolved in 200 μL of water. An additional 2 ml of dimethylformamide was added to aid solubility. The mixture was stirred at room temperature for 30 minutes before acidification to pH 1 with 2N HCl solution and filtration. The solid obtained was washed with ether before dissolving in acetone and concentration under reduced pressure to remove residual organic solvents and afford [4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-imidazo[4,5-c]pyridin-1-yl]-acetic acid (100 mg). 1H NMR (DMSO): δ 8.76 (s, 1H) 8.64 (s, 1H) 8.37 (m, 3H) 7.43 (d, 1H) 5.31 (s, 2H) 4.27 (q, 2H) 1.38 (t, 3H); MS m/z 391.7 (M+1).

Workup

  1. customThe solid obtained
  2. washwas washed with ether
  3. dissolutionbefore dissolving in acetone
  4. concentrationconcentration under reduced pressure
  5. customto remove residual organic solvents

Sources & evidence

ORD record
ord-b8ba36b7e73f4ba095ae6403f402f645
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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