Hydrochloric Acid → HCID 59366204, compound

HRID 532835Notes

Reaction equation

HRID 532835 reaction equation
C[CH:2]([CH:6]([C:26]1[CH:30]=[CH:29][N:28]([CH:31]([CH3:33])[CH3:32])[N:27]=1)[N:7]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[C:15]([O:24][CH3:25])=[CH:16][CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].C1COCC1.[OH-].[Na+].Cl>CO>[CH:31]([N:28]1[CH:29]=[CH:30][C:26]([CH:6]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]3[C:15]([O:24][CH3:25])=[CH:16][CH:17]=[C:18]4[C:23]=3[N:22]=[CH:21][CH:20]=[CH:19]4)[CH2:9][CH2:8]2)[CH2:2][C:3]([OH:5])=[O:4])=[N:27]1)([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66893275HCID 66893275, compound

Product 1

HCID 59366204HCID 59366204, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 35 mL scintillation vial equipped with a magnetic stirrer was charged with (±)-methyl 3-(1-isopropyl-1H-pyrazol-3-yl)-3-[4-(7-methoxyquinolin-8-yl)-1,4-diazepan-1-yl]propanoic acid (450 mg, 1.0 mmol), THF (5 mL), MeOH (5 mL) and 1 N NaOH solution (6 mL, 6.0 mmol). The resulting suspension was stirred at 40° C. overnight (18 h). 2 N HCl (ca. 3 mL) was added to bring the pH to 7 and the mixture extracted with 10% MeOH in CH2Cl2 containing 0.5% aqueous NH4OH (3×50 mL). The combined organic layer was concentrated and dried in vacuo to afford the title compound (360 mg, 82%) as a light yellow foam. MS (ES) m/z 438.4 (M+H+).

Workup

  1. customA 35 mL scintillation vial equipped with a magnetic stirrer
  2. extractionthe mixture extracted with 10% MeOH in CH2Cl2 containing 0.5% aqueous NH4OH (3×50 mL)
  3. concentrationThe combined organic layer was concentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1567c85a2c334faea034bb35a566fd57
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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