Triethylamine → HCID 86587685, compound

HRID 1836639Notes

Reaction equation

HRID 1836639 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH:13]3[CH2:15][CH:14]3[C:16]([OH:18])=O)[CH:10]=2)[NH:5][CH:4]=1)#[N:2].Cl.[CH3:20][N:21](C)[OH:22].Cl.[CH3:25]N(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl>[CH3:25][O:22][N:21]([CH3:20])[C:16]([CH:14]1[CH2:15][CH:13]1[CH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][CH:4]=[C:3]2[C:1]#[N:2])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22638693HCID 22638693, compound

Product 1

HCID 86587685HCID 86587685, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid (0.080 g, 0.33 mmol), N, N-dimethylhydroxylamine hydrochloride (0.065 g, 0.67 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.077 g, 0.40 mmol), triethylamine (0.13 g, 1.33 mmol), and dichloromethane (5 ml) was stirred at ambient temperature for 1 h then diluted further with an additional 10 ml dichloromethane. The solution was washed with 1N hydrochloric acid (1×5 ml), 1N sodium hydroxide (1×5 ml), and brine (1×5 ml) and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo to afford 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid methoxy-methyl-amide (0.075 g, 79%) as a light brown film. 1H-NMR (400 MHz, CDCl3) 7.69 (1H, m), 7.57 (1H, s), 7.22 (1H, d, J=2.7 Hz), 7.11 (1H, d, J=1.52 Hz), 3.69 (3H, s), 3.20 (3H, s), 2.81 (2H, m), 2.10 (1H, m), 1.73 (1H, m), 1.28 (1H, m), 0.91 (1H, m).

Workup

  1. washThe solution was washed with 1N hydrochloric acid (1×5 ml), 1N sodium hydroxide (1×5 ml), and brine (1×5 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa5f88c25a1b4214a2d578d89f0bf8fb
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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