Acetyl chloride → HCID 86696342, compound

HRID 870646Notes

Reaction equation

HRID 870646 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[N:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1>N1C=CC=CC=1>[Br:5][C:6]1[N:10]2[N:11]=[C:12]([NH:15][CH2:16][CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[C:1](=[O:3])[CH3:2])[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86696340HCID 86696340, compound

Product 1

HCID 86696342HCID 86696342, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride [75-36-5] (1.0 mL, 14.1 mmol) was added, in portions, to an ambient temperature solution of N1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-N3-isopropylpropane-1,3-diamine (196.9 mg, 0.6 mmol) in pyridine (6.5 mL), and stirred under N2 blanket for 17 h. Pyridine was evaporated from the reaction mixture and the residue partitioned between aqueous 5% (w/v) sodium bicarbonate and ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and evaporated to afford 219.2 mg of dark oil. LRMS (ESI) m/z 354.1/356.1 [(M+H)]+, calc'd for C14H20BrN5O: 354.25.

Workup

  1. customPyridine was evaporated from the reaction mixture
  2. customthe residue partitioned between aqueous 5% (w/v) sodium bicarbonate and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-bed02777ab2841acbad76887fe69612b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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