Triethylamine → HCID 58697572, compound

HRID 2212975Notes

Reaction equation

HRID 2212975 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C@@H:12]3[CH2:16][CH2:15][CH2:14][C@H:13]3[C:17]([OH:19])=O)[CH:10]=2)[NH:5][CH:4]=1)#[N:2].Cl.[CH3:21][NH:22][O:23][CH3:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl>[CH3:24][O:23][N:22]([CH3:21])[C:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[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:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58697560HCID 58697560, compound

Product 1

HCID 58697572HCID 58697572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of trans-2-(3-Cyano-1H-indol-5-yl)-cyclopentanecarboxylic acid (0.66 g, 2.60 mMol), N,O-dimethylhydroxylamine hydrochloride (0.51 g, 5.20 mMol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.54 g, 2.86 mMol), and dichloromethane (20 mL) was treated with triethylamine (1.05 g, 10.4 mMol) and stirred at ambient temperature for 18 h. The resulting solution was diluted with 30 mL dichloromethane, washed with 1M hydrochloric acid, 1M sodium hydroxide, and brine, dried over sodium sulfate and concentrated in vacuo to give the crude product as a clear oil which was used without further purification (0.51 g, 66%). LC-MS: 1.38 min (2 min gradient); 298.11 (MH)+.

Workup

  1. washwashed with 1M hydrochloric acid, 1M sodium hydroxide, and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8d5278c70184012b2e48ac143beff50
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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