1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[4-Chloro-3-(1-methylpiperidin-4-yl)phenyl]-4-(pyridin-4-yl)naphth-ylacetamide

HRID 1275030Notes

Reaction equation

HRID 1275030 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][C:18]([OH:20])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:44][C:45]1[CH:51]=[CH:50][C:48]([NH2:49])=[CH:47][C:46]=1[CH:52]1[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]1>ClCCl>[Cl:44][C:45]1[CH:51]=[CH:50][C:48]([NH:49][C:18](=[O:20])[CH2:17][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:8][CH:9]=2)=[CH:47][C:46]=1[CH:52]1[CH2:53][CH2:54][N:55]([CH3:58])[CH2:56][CH2:57]1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 221189274-Chloro-3-(1-methylpiperidin-4-yl)anilineHCID 224625334-(Pyridin-4-yl)naphth-1-ylacetic acid

Product 1

HCID 22118907N-[4-Chloro-3-(1-methylpiperidin-4-yl)phenyl]-4-(pyridin-4-yl)naphth-ylacetamideYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4 -(pyridin-4-yl)napth-1-ylacetic acid (D2, 260 mg, 1.0 mmol) in dichloromethane was added 1-hydroxybenzotriazole hydrate (153 mg, 1.0 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (200 mg, 1.0 mnmol) and the mixture stirred for 0.5 h. To the mixture was added dropwise a solution of 4-chloro-3-(1-methylpiperidin-4-yl)aniline (D7, 200 mg, 0.90 mmol) in dichloromethane (3 ml) and stirring continued for 48 h. Purification of the crude by flash chromatography gave the title compound as a white solid (30 mg, 7%).

Workup

  1. stirringstirring
  2. waitcontinued for 48 h
  3. customPurification of the crude by flash chromatography

Sources & evidence

ORD record
ord-f3440b59785c4756958ff20f87e43a92
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

Loading…