Methyl iodide → N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide

HRID 1039023Notes

Reaction equation

HRID 1039023 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@H:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:16][CH3:17].[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH3:28][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@H:15]([NH:18][C:19](=[O:24])[C:20]([F:21])([F:23])[F:22])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86654754(S)-N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide

Product 1

HCID 86654755N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 20 mL cintillation vial was charged with (S)—N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide (60 mg, 0.169 mmol) and dimethylformamide (0.75 mL). Sodium hydride (6.0 mg, 0.25 mmol) was added and the resulting mixture was stirred at room temperature for 15 minutes. Methyl iodide (0.012 mL, 0.193 mmol) was added and the resulting mixture was stirred at room temperature for 1 h. The resulting mixture was then concentrated in-vacuo and purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-50:50 Heptane:EtOAc) to yield N-[3-(1-methyl-1H-indol-2-yl)-propyl]-2-(S)-(2,2,2-trifluoro-acetylamino)-butyramide. 1H NMR (300 MHz, CDCl3) δ7.52 (d, J=7.7 Hz, 1H), 7.25-7.28 (m, 1H), 7.14-7.19 (m, 1H), 7.04-7.10 (m, 1H), 6.26 (s, 1H), 4.31-4.36 (m, 1H), 3.64 (s, 3H), 3.33-3.46 (m, 2H), 2.75-2.82 (m, 2H), 1.80-2.09 (m, 3H), 1.59-1.71 (m, 1H), and 0.87-0.92 (m, 3H); MS (ES+) 370 (M+1).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 h
  2. concentrationThe resulting mixture was then concentrated in-vacuo
  3. custompurified via flash silica gel chromatography (Analogix IF-280

Sources & evidence

ORD record
ord-a28ed6f719624411af634716f4928ac9
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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