2-Bromoethanol → HCID 22025148, compound

HRID 1792773Notes

Reaction equation

HRID 1792773 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:21]=[CH:20][C:13]3[O:14][CH:15]([CH2:18][OH:19])[CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:22]#[N:23])=[C:4]([SH:24])[N:3]=1.[OH:25][CH2:26][CH2:27]Br.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:21]=[CH:20][C:13]3[O:14][CH:15]([CH2:18][OH:19])[CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:22]#[N:23])=[C:4]([S:24][CH2:27][CH2:26][OH:25])[N:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 178510471HCID 178510471, compound

Product 1

HCID 22025148HCID 22025148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 mg (0.09 mmol) of 2-amino-6-sulfanyl-4-[2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry 33 (7), 1014–1017 (1997); 34 (4), 557–563 (1998)], 22 mg (0.18 mmol) of 2-hydroxyethyl bromide and 29 mg (0.35 mmol) of sodium bicarbonate are stirred in 1.5 ml of DMF at room temperature overnight. The reaction solution is purified directly by preparative HPLC on reversed-phase silica gel.

Workup

  1. customThe reaction solution is purified directly by preparative HPLC on reversed-phase silica gel

Sources & evidence

ORD record
ord-8a06105050574671a0aa48f482262b47
Source dataset
uspto-grants-2006_07
Patent number
US07078417B2

Reaction notes

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