Ethanethiol → HCID 17989712, compound

HRID 1271088Notes

Reaction equation

HRID 1271088 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.[CH2:30]([SH:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[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]=1[S:32][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 17989685HCID 17989685, compound

Product 1

HCID 17989712HCID 17989712, compoundYield 46%

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 0.15 mL of ethylmercaptan and 0.280 mg of potassium carbonate. The mixture was heated to reflux for 2 h. The suspension was filtered and the solid was washed with ethyl acetate to gave the title compound (0.220 g, 46%). Mp 80–100° C., 1H NMR (DMSO-d6) 8.8 (1H, d, 3 Hz), 859 (1H, d, 6 Hz), 8.37 (1H, s, NH), 7.98 (1H, d, 6 Hz, 3 Hz), 7.92 (1H, t, 3 Hz), 7.86 (1H, s), 7.46 (1H, d, 9 Hz, 3 Hz), 7.40 (1H,s), 7.27(2H, m), 7.04(1H, d, 9 Hz), 3.12 (2H, q, 6 Hz), 1.47 (3H, t, 6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-8432b9eae8364309b128e74bcbe4a0e7
Source dataset
uspto-grants-2007_04
Patent number
US07205301B2

Reaction notes

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