Pyridine → HCID 24963389, compound

HRID 655293Notes

Reaction equation

HRID 655293 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.Cl.[F:11][C:12]1(CC(O)=O)C=CC2N=CC=CC=2[CH2:13]1.N1C=CC=[CH:28][CH:27]=1.C1(N=[C:39]=[N:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)CCCCC1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:13]([CH:12]([F:11])[C:44]3[CH:45]=[C:46]4[C:41](=[CH:42][CH:43]=3)[N:40]=[CH:39][CH:28]=[CH:27]4)=[N:9][N:8]=2)[N:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 1007873-Chloro-6-hydrazinopyridazineHCID 68706254HCID 68706254, compound

Product 1

HCID 24963389HCID 24963389, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (6-chloro-pyridazin-3-yl)-hydrazine (233 mg, 1.6 mmol) and 6-fluoro-quinolin-6-yl-acetic acid hydrochloride (3.90 mg, 1.6 mmol) in dichloromethane (22 mL) and pyridine (1.6 mmol, 126 mg) at ambient temperature was added dicyclohexylcarbodiimide (333 mg, 1.6 mmol). After stirring at room temperature for 18 hours the formed precipitate was filtered off, washed with dichloromethane and dried in vacuo and then taken up in acetic acid (15 mL) and heated for 6 hours at 55° C. After such time the mixture was concentrated onto silica gel in vacuo and purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10) to return the title compound as a yellow foam (138 mg, 0.44 mmol, 28% yield). Analytical data presented in Table 1.

Workup

  1. filtrationwas filtered off
  2. washwashed with dichloromethane
  3. customdried in vacuo
  4. temperatureheated for 6 hours at 55° C
  5. concentrationAfter such time the mixture was concentrated onto silica gel in vacuo
  6. custompurified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10)

Sources & evidence

ORD record
ord-c65355f8252547a98291be338ea9bcd0
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

Loading…