Tetrahydrofuran → HCID 86698698, compound

HRID 1054701Notes

Reaction equation

HRID 1054701 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([O:14]C)=[O:13])=[CH:8][NH:9]2)=[CH:5][C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)=[C:18]([O:29][CH3:30])[CH:17]=1.O1CCCC1.[OH-].[Na+]>CO>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([OH:14])=[O:13])=[CH:8][NH:9]2)=[CH:5][C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)=[C:18]([O:29][CH3:30])[CH:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86698699HCID 86698699, compound

Product 1

HCID 86698698HCID 86698698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (S)-methyl 6-chloro-5-(3-methoxy-4-(pyrrolidin-2-ylmethoxy)phenyl)-1H-indole-3-carboxylate hydrochloride (22.6 mg, 0.050 mmol) in methanol (0.26 mL) was added tetrahydrofuran (0.26 mL) and sodium hydroxide (1 N in water, 0.26 mL, 0.26 mmol). The mixture was then sealed and heated to 65° C. After 41 h, the mixture was allowed to cool to 23° C., concentrated in vacuo, diluted with water (1 mL), then acidified to pH 7.5 with hydrochloric acid (1 N in water). The solid was filtered and purified by reverse phase HPLC to provide the title compound. MS (ES+) 401.2 (M+H)+. HPLC retention time: 1.44 min, Waters XBridge C18, 5 μm, 4.6×50 mm, 0.03% NH4OH, 5-95% acetonitrile in water gradient over 4.0 min, hold at 95% acetonitrile in water to 5.0 min, flow 2.0 mL/min.

Workup

  1. customThe mixture was then sealed
  2. temperatureto cool to 23° C.
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water (1 mL)
  5. filtrationThe solid was filtered
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-8f67bd9525c64b079246c0238e99e568
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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