Hydrochloric Acid → HCID 73673718, compound

HRID 2401646Notes

Reaction equation

HRID 2401646 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].O.Cl>C1COCC1>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 74222692HCID 74222692, compound

Product 1

HCID 73673718HCID 73673718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

67 mg of methyl 8-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}-amino)octanoate Example 16 (0.15 mmol, 1 equivalent) were dissolved in 2.5 ml of THF, and 0.3 ml of 1 M lithium hydroxide solution in water (0.3 mmol, 2 equivalents) was added. The mixture was stirred at RT overnight and then acidified with 1 M aq. hydrochloric acid and concentrated. The residue was dissolved in methanol/acetonitrile and purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). this gave 22 mg (34% of theory; purity: 100%) of the title compound.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol/acetonitrile
  3. custompurified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-bc1d3eca6aab4887847503936a4e403b
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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