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Triethylamine → N-[3-(1-Methylpiperidin-4-yl)indol-5-yl]-4-(pyridin-4-yl)naphth-1-ylacetamide

HRID 1936721
Notes
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Reaction equation

HRID 1936721 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](O)=[O:19])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[CH:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]1.C(N(CC)CC)C>ClCCl>[CH3:43][N:40]1[CH2:41][CH2:42][CH:37]([C:31]2[C:30]3[C:34](=[CH:35][CH:36]=[C:28]([NH:27][C:18](=[O:19])[CH2:17][C:10]4[C:11]5[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=5)[C:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)=[CH:8][CH:9]=4)[CH:29]=3)[NH:33][CH:32]=2)[CH2:38][CH2:39]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amineHCID 224625334-(Pyridin-4-yl)naphth-1-ylacetic acid

Product 1

HCID 17898954N-[3-(1-Methylpiperidin-4-yl)indol-5-yl]-4-(pyridin-4-yl)naphth-1-ylacetamideYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A stirred suspension of 4-(pyridin-4-yl)naphth-1-ylacetic acid (D7, 0.18 g, 0.7 mmole) in dichloromethane (15 ml) was treated with oxalyl chloride (0.18 ml, 2.1 mmole), then stirred at room temperature for 3 hours, before evaporating to dryness. The solid residue was suspended in dichloromethane (15 ml), cooled to 0° C. and treated with a solution of 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole (D2, 0.13 g, 0.56 mmole) in dichloromethane (15 ml). The mixture was stirred at 0° for 1 hour and then a solution of triethylamine (0.25 ml) in dichloromethane (5 ml) was added dropwise. The mixture was allowed to warm to room temperature and stir overnight, then evaporated to dryness and the residue subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:5:0.5 to 100:10:1 gradient elution) to afford the title compound as a pale cream powder (0.04 g).

Workup

  1. custombefore evaporating to dryness
  2. temperaturecooled to 0° C.
  3. stirringThe mixture was stirred at 0° for 1 hour
  4. temperatureto warm to room temperature
  5. stirringstir overnight
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a4c5656425a74981b8f84ad03bc2a58c
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06391891B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes