Ethanol → 2-Chloro-N-[6-[8-(1-oxido-pyridin-1-ium-4-yl)-3,8-diazaspiro[4.5]decane-3-carbonyl]-2,3-dihydro-1H-inden-1-yl]-benzamide

HRID 1253753Notes

Reaction equation

HRID 1253753 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][CH:19]2[NH:22][C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[CH:15][CH:14]=1)=[O:12].CCN(C(C)C)C(C)C.Cl[C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1.CC[OH:50]>>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:23]([NH:22][CH:19]1[C:20]2[C:16](=[CH:15][CH:14]=[C:13]([C:11]([N:2]3[CH2:1][C:5]4([CH2:10][CH2:9][N:8]([C:42]5[CH:47]=[CH:46][N+:45]([O-:50])=[CH:44][CH:43]=5)[CH2:7][CH2:6]4)[CH2:4][CH2:3]3)=[O:12])[CH:21]=2)[CH2:17][CH2:18]1)=[O:31]

Participants

5

Reactant 4

HCID 702EthanolHCID 122884-ChloropyridineHCID 81531DiisopropylethylamineHCID 59505509N-(6-(2,8-Diazaspiro[4.5]decane-2-carbonyl)-2,3-dihydro-1H-inden-1-yl)-2-chlorobenzamide

Product 1

HCID 595056002-Chloro-N-[6-[8-(1-oxido-pyridin-1-ium-4-yl)-3,8-diazaspiro[4.5]decane-3-carbonyl]-2,3-dihydro-1H-inden-1-yl]-benzamideYield 23%

Conditions

Temperature
130 °C

Procedure

A stirred mixture of N-(6-(2,8-diazaspiro[4.5]decane-2-carbonyl)-2,3-dihydro-1H-inden-1-yl)-2-chlorobenzamide (350 mg, 0.799 mmol, 1 eq.), DIPEA (0.34 ml, 1.99 mmol, 2.5 eq.) and 4-chloropyridine (103 mg, 0.799 mmol, 1 eq.) in EtOH (7 ml) was heated at 130° C. for 72 h. The solvent was removed and the crude material was purified by column chromatography (silica gel, 3-5% MeOH/MC) to afford the final product as a light brown solid. Yield: 23% (100 mg, 0.19 mmol).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by column chromatography (silica gel, 3-5% MeOH/MC)

Sources & evidence

ORD record
ord-bbb544471bf84e4dae33954fb4627a2a
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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