Hydrochloric Acid → HCID 90134687, compound

HRID 1506800Notes

Reaction equation

HRID 1506800 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].Cl>O1CCOCC1>[Br:1][C:2]1[N:3]=[N:4][C:5]([NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:10]([Cl:9])[CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 2488523,6-Dibromopyridazine

Product 1

HCID 90134687HCID 90134687, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3,6-Dibromopyridazine (1 g, 4.20 mmol) was added to a solution of 3-chloroaniline (0.536 g, 4.20 mmol) in 1,4-dioxane (10 mL) followed by 4M HCl in 1,4-dioxane (6 mL, 24 mmol). The mixture was refluxed for 3 h. The slurry obtained was filtered, and the crude product was purified by preparative HPLC to afford the title compound 21D (0.3 g, 23%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 9.67 (s, 1H), 8.09 (t, J=1.8 Hz, 1H), 7.7 (d, J=9.0 Hz, 1H), 7.5 (dd, J1=9.0 Hz, J2=0.9 Hz, 1H), 7.35 (t, J=8.1 Hz, 1H), 7.12 (d, J=9.6 Hz, 1H), 7.05 (dd, J1=8.1 Hz, J2=0.9 Hz, 1H). ESI-MS m/z: 284 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe slurry obtained
  3. filtrationwas filtered
  4. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4cfcc3ed83a0419d9dc40c607883da5b
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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