Water → HCID 68291635, compound

HRID 1507935Notes

Reaction equation

HRID 1507935 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[CH2:15]([NH2:18])[CH2:16][CH3:17].C(N(C(C)C)CC)(C)C.O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:18][CH2:15][CH2:16][CH3:17])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291635HCID 68291635, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 137 mg, 0.5 mmol), n-propylamine (123 mL, 1.500 mmol) and diisopropylethylamine (0.349 mL, 2.000 mmol) in N-methylpyrrolidinone (1.5 mL) was heated to 105° C. for 0.75 hr. After cooling to rt, water (15 ml) was added and the resulting suspension was stirred at rt for 1 hr. The suspension was filtered and the filter cake was dried. The filter cake was rinsed with hexane and dried to afford the title compound (120 mg, 0.382 mmol, 76% yield) as a tan solid. HPLC (condition M): retention time=2.56 min.; LCMS (ES+) m/z: 297.00/299.00; 1H NMR (400 MHz, MeOD) δ ppm 1.09 (t, J=7.4 Hz, 3 H), 1.72-1.83 (m, 2 H), 3.70 (t, J=6.9 Hz, 2 H), 7.01 (d, J=1.8 Hz, 1 H), 7.60 (d, J=1.8 Hz, 1 H), 8.09 (s, 1 H).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe suspension was filtered
  3. customthe filter cake was dried
  4. washThe filter cake was rinsed with hexane
  5. customdried

Sources & evidence

ORD record
ord-ce560fc728c0439bb71908f61640889a
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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