Methanesulfonyl chloride → HCID 68291890, compound

HRID 877723Notes

Reaction equation

HRID 877723 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]3([CH3:18])[CH3:17])=[C:8]([C:19]([NH2:21])=[O:20])[CH:7]=[N:6][N:5]2[CH:22]=1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:13][C:12]3([CH3:18])[CH3:17])=[C:8]([C:19]([NH2:21])=[O:20])[CH:7]=[N:6][N:5]2[CH:22]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68290851HCID 68290851, compound

Product 1

HCID 68291890HCID 68291890, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cloudy solution of (+/−)-6-bromo-4-(3,3-dimethylpiperidin-4-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide from Step 3 of Example 1 (300 mg, 0.625 mmol) and DIPEA (0.436 mL, 2.499 mmol) in dichloromethane (10 mL) at 0° C. was added methanesulfonyl chloride (0.058 mL, 0.750 mmol) and the resulting mixture was stirred at rt for 3 h. Reaction was diluted with dichloromethane (150 mL), washed with water and brine, dried over MgSO4, filtered and concentrated to afford the title compound as a tan solid (94% yield). HPLC (condition B): retention time=3.11 min. LCMS (condition H): m/z 444, 446 +ve.

Workup

  1. customReaction
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f7cfb60cf212453bbace0f4d9a87b622
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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