Sodium Azide → HCID 17989714, compound

HRID 1271089Notes

Reaction equation

HRID 1271089 reaction equation
[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:16]=3)[CH:12]=[CH:11][N:10]=2)[N:5]=[CH:6][C:7]=1Cl.[N-:30]=[N+:31]=[N-:32].[Na+]>C(#N)C>[N:30]([C:7]1[CH:6]=[N:5][N:4]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:16]=3)[CH:12]=[CH:11][N:10]=2)[C:3](=[O:29])[C:2]=1[Cl:1])=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 17989685HCID 17989685, compound

Product 1

HCID 17989714HCID 17989714, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in acetonitrile (10 mL) was added of 0.09 g of sodium azide. The mixture was heated to reflux for 4 h. The suspension was filtered to give the title compound as a solid (0.280 g, 95%). Mp 184–186° C., 1H NMR (DMSO-d6) 10.1 (1H, s, NH), 8.75 (1H, d, 6 Hz), 8.67 (1H, d, 3 Hz), 8.28 (1H, s), 8.27 (1H, s), 8.18(1H, dd, 1 Hz, 3 Hz), 7.97 (1H, m), 7.65 (1H, dd), 7.57(1H, d, 6 Hz), 7.25 (1H, t, 9 Hz), 6.94 (1H, dd).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-464f2b00e0364554b46bd8380a131b57
Source dataset
uspto-grants-2007_04
Patent number
US07205301B2

Reaction notes

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