Water → HCID 68291682, compound

HRID 1507954Notes

Reaction equation

HRID 1507954 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]([SH:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([S:17][CH2:15][CH3:16])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291682HCID 68291682, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 5 g, 18.21 mmol), ethanethiol (1.482 mL, 20.04 mmol) and potassium carbonate (5.03 g, 36.4 mmol) in NMP (volume: 60 mL) was stirred at rt for 18 hr. Water (500 ml) was added and the resulting suspension was stirred at rt for 1 hr. The suspension was filtered and the filter cake was air dried. The solid obtained was then washed with hexane and dried to afford a dark yellow solid. This solid was dissolved in warm EtOAc (200 ml) and decolorizing carbon was added. The mixture was allowed to stand for 10 minutes. The mixture was filtered through celite and the filter cake was washed thoroughly with warm EtOAc. The filtrate was concentrated and dried under high vacuum to afford the title compound (3.56 g, 11.86 mmol, 65.1% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (t, J=7.5 Hz, 3 H) 3.11 (q, J=7.4 Hz, 2 H) 5.98 (brs, 1 H) 7.03 (d, J=1.8 Hz, 1 H) 7.83 (d, J=1.8 Hz, 1 H) 7.95 (brs, 1 H) 8.66 (s, 1 H). LCMS (M+H)=299.95/301.95.

Workup

  1. stirringthe resulting suspension was stirred at rt for 1 hr
  2. filtrationThe suspension was filtered
  3. customdried
  4. customThe solid obtained
  5. washwas then washed with hexane
  6. customdried
  7. customto afford a dark yellow solid
  8. additionwas added
  9. waitto stand for 10 minutes
  10. filtrationThe mixture was filtered through celite
  11. washthe filter cake was washed thoroughly with warm EtOAc
  12. concentrationThe filtrate was concentrated
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-512ccc30f113407bbf1e7db0bd3378fd
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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