Dimethyl Sulfone → HCID 69812205, compound

HRID 1916146Notes

Reaction equation

HRID 1916146 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].[NH:39]1[CH2:43][CH2:42][C@@H:41]([OH:44])[CH2:40]1.CS(C)(=O)=O>O1CCOCC1>[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][NH:24][C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14]([N:39]3[CH2:43][CH2:42][C@@H:41]([OH:44])[CH2:40]3)[N:13]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 2759337(R)-3-PyrrolidinolHCID 58177355HCID 58177355, compound

Product 1

HCID 69812205HCID 69812205, 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, (R)-pyrrolidin-3-ol was used to displace the methylsulfone similar to examples above and the de-protection step was similar to step 5, Example 76, to give (R)-1-[4-((R)-1-methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-pyrrolidin-3-ol. MS: (ES+): 459

Sources & evidence

ORD record
ord-76a00e1927f7446194ee1da66ac05a7f
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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