Chlorobenzene → HCID 58270296, compound

HRID 2362613Notes

Reaction equation

HRID 2362613 reaction equation
[CH2:1]([O:3][CH:4]([O:17][CH2:18][CH3:19])[CH2:5][C:6]#[C:7][C:8]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH3:16])[CH:12]=1)=[O:9])[CH3:2].ClC1C=CC=CC=1.[N:27]([CH:30]([C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][C:36]([O:42][CH2:43][CH2:44][O:45][CH3:46])=[CH:35]2)[CH3:31])=[N+:28]=[N-:29]>>[CH2:18]([O:17][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][C:6]1[N:29]=[N:28][N:27]([CH:30]([C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[N:38]=[CH:37][C:36]([O:42][CH2:43][CH2:44][O:45][CH3:46])=[CH:35]3)[CH3:31])[C:7]=1[C:8]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH3:16])[CH:12]=1)=[O:9])[CH3:19]

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 58270279HCID 58270279, compoundHCID 66617149HCID 66617149, compound

Product 1

HCID 58270296HCID 58270296, compound

Conditions

Temperature
100 °C

Procedure

5,5-diethoxy-N-(3-methylisothiazol-5-yl)pent-2-ynamide (0.700 g, 2.5 mmol) was dissolved in chlorobenzene (2.5 mL, 2.5 mmol), and to the solution was added 6-(1-azidoethyl)-3-(2-methoxyethoxy)quinoline (0.68 g, 2.5 mmol). The mixture was heated to 100° C. overnight and then increased to 110° C. for 5.5 h. The reaction was concentrated in vacuo. The compound was purified via MPLC (eluting with 0-40% EtOAc in hexanes) to yield 5-(2,2-diethoxyethyl)-3-(1-(3-(2-methoxyethoxy)quinolin-6-yl)ethyl)-N-(3-methylisothiazol-5-yl)-3H-1,2,3-triazole-4-carboxamide.

Workup

  1. temperatureincreased to 110° C. for 5.5 h
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe compound was purified via MPLC (eluting with 0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-77fd122eeeb3431b9bc8c2c8d423f434
Source dataset
uspto-grants-2014_04
Patent number
US08691838B2

Reaction notes

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