Acetyl chloride → HCID 57933014, compound

HRID 1432668Notes

Reaction equation

HRID 1432668 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([NH:22][CH3:23])=[N:19][C:18]=3[CH3:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([N:22]([CH3:23])[C:32](=[O:34])[CH3:33])=[N:19][C:18]=3[CH3:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86620093HCID 86620093, compound

Product 1

HCID 57933014HCID 57933014, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg of N-{5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-thiazol-2-yl}-methylamine (0.17 mmol) and 86 mg of triethylamine (0.85 mmol) are dissolved in 3.0 ml of CH2Cl2 and 16 mg of acetylchloride (0.2 mmol) is added. The vial is capped with a Teflon® lined cap and shaken at room temperature for 2 h. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1 and Hexane:AcOEt=2:1) to give 33.8 mg of the title compound. Yield 50%: mass spectrum (m/e): 386 (M+1); 1H-NMR (CDCl3): 7.03 (s, 1H), 3.79 (s, 3H), 3.47 (m, 1H), 2.54 (s, 3H), 2.47 (s, 3H), 2.46 (s, 3H), 2.31 (s, 3H), 1.86 (m, 4H), 0.91 (t, 6H, J=7.4 Hz).

Workup

  1. customlined cap
  2. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-97cdaa5baf964c5fa67a52d7d4315d45
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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