Dimethyl Sulfone → HCID 69810608, compound

HRID 1916124Notes

Reaction equation

HRID 1916124 reaction equation
CS([C:5]1[N:10]=[C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([S:18]([CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH2:13]2)[C:8]([C:25]2[N:26]=[C:27]3[CH:33]=[CH:32][N:31](COCC[Si](C)(C)C)[C:28]3=[N:29][CH:30]=2)=[CH:7][N:6]=1)(=O)=O.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.CS(C)(=O)=O>O1CCOCC1>[CH3:23][CH:22]([CH3:24])[CH2:21][S:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([NH:11][C:9]2[C:8]([C:25]3[N:26]=[C:27]4[CH:33]=[CH:32][NH:31][C:28]4=[N:29][CH:30]=3)=[CH:7][N:6]=[C:5]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[N:10]=2)[CH2:13]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 8083MorpholineHCID 69815196HCID 69815196, compound

Product 1

HCID 69810608HCID 69810608, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a dioxane solution of {2-methanesulfonyl-5-[5-(2-trimethysilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine from Example 3, step 1, morpholine was used to displace the methylsulfone similar to examples above and the de-protection step was similar to step 5 of Example 76 to give [(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-[2-morpholin-4-yl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine. MS (ES+): 501.

Sources & evidence

ORD record
ord-5cb6e48044e141a9a8efece96b92e38c
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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