Triethylamine → HCID 57933082, compound

HRID 1432669Notes

Reaction equation

HRID 1432669 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.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>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])[S:33]([CH3:32])(=[O:35])=[O:34])=[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 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86620093HCID 86620093, compound

Product 1

HCID 57933082HCID 57933082, compoundYield 75.1%

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 23 mg of methanesulfonyl chloride (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 to silica-gel chromatography (Hexane:AcOEt=2:1) to give 53.8 mg of the title compound. Yield 75%. mass spectrum (m/e): 422 (M+1); 1H-NMR (CDCl3): 6.96 (s, 1H), 3.60 (s, 3H), 3.34 (m, 1H), 3.19 (s, 3H), 2.56 (s, 3H), 2.48 (s, 3H), 2.29 (s, 3H), 1.86 (m, 4H), 0.90 (t, 6H, J=7.4 Hz).

Workup

  1. customlined cap
  2. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-605ca8ae6d7547d4bfb720f8324953e2
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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