Hydrochloric Acid → HCID 71062314, compound

HRID 529036Notes

Reaction equation

HRID 529036 reaction equation
[CH2:1]([N:5]([CH2:34][CH2:35][CH2:36][CH3:37])[C:6]1[N:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][C:13]=2[C:22]([N:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([N:5]([CH2:34][CH2:35][CH2:36][CH3:37])[C:6]1[N:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[C:22]([N:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71062264HCID 71062264, compound

Product 1

HCID 71062314HCID 71062314, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(6-(dibutylamino)pyridin-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (75 mg, 0.15 mmol) in THF (1.0 mL) and MeOH (1.0 mL) was added 2N NaOH (0.75 mL, 1.50 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. At 0° C., the reaction mixture was neutralized to pH 4-5 with 1N HCl. The solution was extracted with EtOAc (3×) and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (69 mg, 95%). MS(ESI+) m/z 486.4 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customAt 0° C.
  3. extractionThe solution was extracted with EtOAc (3×)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1881d95c4b543c8a142f95914befbf7
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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