Water → HCID 46836603, compound

HRID 474219Notes

Reaction equation

HRID 474219 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[N:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:17][N:16]=3)[CH:10]=2)[N:6]=[C:5]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])[CH:4]=[CH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:44][CH3:45].O>CN(C=O)C>[CH2:44]([N:26]1[CH2:25][CH2:24][CH:23]([CH2:22][O:21][C:18]2[CH:17]=[N:16][C:15]([C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[CH2:8][N:7]3[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:29]4[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=4)[C:32]#[N:33])=[N:6]3)=[N:20][CH:19]=2)[CH2:28][CH2:27]1)[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl Bromide2×HCID 10796Cesium carbonateHCID 46836198HCID 46836198, compound

Product 1

HCID 46836603HCID 46836603, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.21 mmol) of 3-(6-oxo-1-{3-[5-(piperidin-4-ylmethoxy)pyrimidin-2-yl]benzyl}-1,6-dihydropyridazin-3-yl)benzonitrile are dissolved in 3 ml of DMF, 204 mg (0.63 mmol) of caesium carbonate and 16 μl (0.21 mmol) of bromoethane are added. The reaction mixture is stirred at room temperature for 15 h, a further 16 μl (0.21 mmol) of bromoethane are added, and the mixture is stirred at room temperature for a further 24 h. Water is added to the reaction mixture, which is then extracted with dichloromethane, dried and evaporated. The crude mixture is purified by means of preparative HPLC.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 24 h
  2. extractionis then extracted with dichloromethane
  3. customdried
  4. customevaporated
  5. customThe crude mixture is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-d751c59d5c674ad2af3650fe1a920ed3
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

Loading…