Hydrochloric Acid → HCID 54759711, compound

HRID 538869Notes

Reaction equation

HRID 538869 reaction equation
[CH3:1][N:2]([CH3:33])[CH:3]([CH2:31][CH3:32])[CH:4]([C:10]1[CH:30]=[CH:29][C:13]2[N:14]=[C:15]([NH:17][CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24]C)=[O:23])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][N:2]([CH3:33])[CH:3]([CH2:31][CH3:32])[CH:4]([C:10]1[CH:30]=[CH:29][C:13]2[N:14]=[C:15]([NH:17][CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 54760071HCID 54760071, compound

Product 1

HCID 54759711HCID 54759711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of methyl 3-(((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]-thiazol-2-yl)amino)methyl)benzoate (18 mg, 0.037 mmol) in 500 μL THF was treated with LiOH (10 mg, 0.238 mmol, 6.5 equiv) in 500 μL water. This was heated at 50° C. overnight. Afterwards the reaction was neutralized with 240 μL of 1N HCl and concentrated in vacuo. The residue was purified by prep-TLC using a 1 mm silica, plate eluting twice with 20% MeOH/DCM to provide 3-(((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)methyl)benzoic acid. MS ESI: m/z 462.21 [M−1+].

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified
  3. washeluting twice with 20% MeOH/DCM

Sources & evidence

ORD record
ord-2b38f613104d467987241947fa97dd49
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

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