Ethylamine → HCID 44481978, compound

HRID 1972128Notes

Reaction equation

HRID 1972128 reaction equation
[C:1]1([CH:7]2[C:16]3[C:11]4=[C:12]([CH:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][CH2:23][N:10]4[CH2:9][CH2:8]2)[CH:13]=[C:14]([CH2:17][C:18]([OH:20])=O)[CH:15]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:30]([NH2:32])[CH3:31].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH2:30]([NH:32][C:18](=[O:20])[CH2:17][C:14]1[CH:13]=[C:12]2[C:11]3=[C:16]([CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8][CH2:9][N:10]3[CH2:23][CH2:22][CH:21]2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:15]=1)[CH3:31]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58453039HCID 58453039, compound

Product 1

HCID 44481978HCID 44481978, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)acetic acid (16), (85 mg, 0.229 mmol) in dichloromethane (10 mL) were added Ethyl amine (0.015 mL, 0.229 mmol), EDCl (103 mg, 0.538 mmol), followed by HOBt (72 mg, 0.538 mmol) under argon at 0° C. The reaction mixture was then stirred at room temperature for overnight. The reaction was quenched with water (30 mL). The residue was isolated in a typical aqueous workup and purified by MPLC (medium pressure liquid chromatography) using silica gel column with 5% MeOH:CH2Cl2 to give N-ethyl-2-(1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)acetamide (371), (27 mg, 29%).

Workup

  1. customThe reaction was quenched with water (30 mL)
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by MPLC (medium pressure liquid chromatography)

Sources & evidence

ORD record
ord-92cf6ff5336248e1a8ff028d8246856d
Source dataset
uspto-grants-2013_04
Patent number
US08431702B2

Reaction notes

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