Dicyclohexylcarbodiimide → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[N:10]1[C:19]2[C:14](=[CH:15][C:16]([CH2:20][C:21](O)=O)=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:21]([CH2:20][C:16]3[CH:15]=[C:14]4[C:19](=[CH:18][CH:17]=3)[N:10]=[CH:11][CH:12]=[CH:13]4)=[N:9][N:8]=2)[N:7]=1Participants
Procedure
To a suspension of (6-chloro-pyridazin-3-yl)-hydrazine (1.62 g, 11.2 mmol) and 6-quinoline acetic acid (2.1 g, 11.2 mmol) in dichloromethane (150 mL) at ambient temperature was added dicyclohexylcarbodiimide (2.3 g, 11.2 mmol). After stirring at room temperature for 4.5 hours the formed precipitate was filtered off, washed with dichloromethane and dried in vacuo to return quinolin-6-yl-acetic acid N′-(6-chloro-pyridazin-3-yl)-hydrazide which also contained dicyclohexylurea. This mixture was then taken up in acetic acid (250 mL) and heated for 4 hours at 50° C. After such time the mixture was concentrated onto silica gel in vacuo and purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-97:3) to return the title compound as a white solid (3.35 g, 11.1 mmol, 99% yield). Analytical data presented in Table 1.
Workup
- filtrationwas filtered off
- washwashed with dichloromethane
- customdried in vacuo
- temperatureheated for 4 hours at 50° C
- concentrationAfter such time the mixture was concentrated onto silica gel in vacuo
- custompurified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-97:3)
Sources & evidence
- ORD record
- ord-a55b1fbc54364a179eeb711badb22abd
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071581B2
Reaction notes
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