Tetrahydrofuran → HCID 86698698, compound

HRID 338358Notes

Reaction equation

HRID 338358 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 (1N 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 (1N 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-7c6234314077432688f200e5f8e95fac
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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