Hydrochloric Acid → HCID 21071629, compound

HRID 1666857Notes

Reaction equation

HRID 1666857 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:19]=1)=[O:4].Cl>C1COCC1.[OH-].[Na+]>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]([F:27])([F:29])[F:28])[CH:19]=1)([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21071639HCID 21071639, compound

Product 1

HCID 21071629HCID 21071629, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Combine N-(2-(5-methoxycarbonyl-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine (200 mg, 0.5 mmol) in 50 mL THF and 1 mL 3 N NaOH. Reflux the mixture overnight, treat with 0.7 mL 5 N HCl and concentrate to dryness. Chromatograph to give the title compound: ISMS 393 (M+1); Analysis for C20H19F3N2O3 CF3COOH 1.2C7H8 2.1H2O: calcd: C, 55.76; H, 5.20; N, 4.28. found: C, 55.51; H, 5.47; N, 4.50.

Workup

  1. temperatureReflux the mixture overnight
  2. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-90522197c3d74a6e9729c8ffc0305c39
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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