Dimethyl Sulfone → HCID 58177221, compound

HRID 1916143Notes

Reaction equation

HRID 1916143 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24](COCC[Si](C)(C)C)[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14](S(C)(=O)=O)[N:13]=2)[CH2:6]1)(=[O:4])=[O:3].[CH3:39][N:40]([CH3:47])[CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.CS(C)(=O)=O>O1CCOCC1>[CH3:39][N:40]([CH3:47])[CH:41]1[CH2:46][CH2:45][N:44]([C:14]2[N:13]=[C:12]([NH:11][C@H:7]3[CH2:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6]3)[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][NH:24][C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=2)[CH2:43][CH2:42]1

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 417391N,N-Dimethylpiperidin-4-amineHCID 58177355HCID 58177355, compound

Product 1

HCID 58177221HCID 58177221, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a dioxane solution of ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methanesulfonyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine derived from Example 84, step 1, dimethylpiperidin-4-ylamine was used to displace the methylsulfone similar to examples above and the de-protection step was similar to step 5, Example 76, to give [2-(4-dimethylamino-piperidin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine. MS: (ES+): 500.

Sources & evidence

ORD record
ord-45df42a759c8485aa1ede6bc492b4b05
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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