Methanesulfonyl chloride → HCID 57929943, compound

HRID 1929998Notes

Reaction equation

HRID 1929998 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:26]2[CH2:31][CH2:30][N:29]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57929906HCID 57929906, compound

Product 1

HCID 57929943HCID 57929943, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2 °C

Procedure

A mixture of 4-(2,4-difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-(piperidin-4-yl)thiazole (0.25 g, 0.57 mmol, Example #Q.1.1), TEA (0.32 mL, 2.3 mmol) and DCM (5 mL) was cooled to about 0-4° C. Methanesulfonyl chloride (0.044 mL, 0.57 mmol) was added. The reaction mixture was stirred at about 04° C. for about 1 h. The reaction was quenched with saturated aqueous Na2CO3 solution. The aqueous layer was extracted with DCM (200 mL). The organic layer was dried over Na2SO4, decanted, and concentrated. The crude product was purified by RP-HPLC (Table 1, Method e) to give the title compound (0.14 g, 48%): LC/MS (Table 1, Method a) Rt=2.49 min; MS m/z: 519.2 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous Na2CO3 solution
  2. extractionThe aqueous layer was extracted with DCM (200 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated
  6. customThe crude product was purified by RP-HPLC (Table 1, Method e)

Sources & evidence

ORD record
ord-05bfc60627b2426bb102a7e58a426f00
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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