Ethanolamine → HCID 58046394, compound

HRID 2046388Notes

Reaction equation

HRID 2046388 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[N:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:11]=1.C(OCC)(=O)C.O>O1CCOCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[CH:11]=[C:6]([NH:4][CH2:3][CH2:1][OH:2])[N:7]=[N:8][CH:9]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 700Ethanolamine2×HCID 962WaterHCID 8857Ethyl AcetateHCID 58046417HCID 58046417, compound

Product 1

HCID 58046394HCID 58046394, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Ethanolamine (4.82 mL, 80 mmol) was added to a stirred mixture of 3-chloro-5-(4-fluorophenyl)pyridazine (2.08 g, 9.97 mmol) in Dioxane (40 mL) in a sealed tube. The mixture was heated to 120° C. overnight, treated with additional ethanolamine (1.2 mL, 20 mmol), and heated to 150° C. for 2 h. The mixture was cooled and poured into ethyl acetate (100 mL) and water (100 mL). The precipitate was filtered and dried to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.76 (d, 1H); 7.78 (dd, 2H); 7.36 (t, 2H); 7.02 (d, 1H); 6.85 (t, 1H); 4.78 (t, 1H); 3.58 (q, 2H); 3.45 (q, 2H). LRMS (APCI) calc'd for (C12H13FN3O) [M+H]+, 234.1. found 234.1.

Workup

  1. temperatureheated to 150° C. for 2 h
  2. temperatureThe mixture was cooled
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-3122348ec4b240bb87cc0ad1e3db917e
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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