Sulfuric Acid → 4-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline-7-carboxamide

HRID 40186Notes

Reaction equation

HRID 40186 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][O:17][C:18]4[C:27]5[C:22](=[CH:23][C:24]([C:28]#[N:29])=[CH:25][CH:26]=5)[N:21]=[CH:20][CH:19]=4)=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:31]>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][O:17][C:18]4[C:27]5[C:22](=[CH:23][C:24]([C:28]([NH2:29])=[O:31])=[CH:25][CH:26]=5)[N:21]=[CH:20][CH:19]=4)=[N:14][N:15]=3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 250651324-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline-7-carbonitrile

Product 1

HCID 250651334-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline-7-carboxamide

Conditions

Temperature
90 °C

Procedure

A mixture of 4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline-7-carbonitrile (0.300 g, 0.793 mmol) and SULFURIC ACID (3.00 ml, 56.3 mmol) was heated at 90° C. for 30 min. Quenched onto ice and sodium bicarbonate. Isolated solid by filtration and purified on RPHPLC. Fractions containing product were treated with 9% sodium carbonate. Removed volatiles. Product crashed out and was isolated by filtraton. MS m/z=397.1 [M+1]+. Calc'd for C22H16N6O2: 396.4.

Workup

  1. customQuenched onto ice and sodium bicarbonate
  2. customIsolated solid
  3. filtrationby filtration
  4. custompurified on RPHPLC
  5. additionFractions containing product
  6. additionwere treated with 9% sodium carbonate
  7. customwas isolated by filtraton

Sources & evidence

ORD record
ord-c787048be0dd42768d6fd89707f00b29
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

Loading…