Dimethyl Sulfone → HCID 69811700, compound

HRID 1916151Notes

Reaction equation

HRID 1916151 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]([CH3:44])[CH2:41][CH2:42][NH2:43].CS(C)(=O)=O>O1CCOCC1>[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][NH:43][C:14]1[N:13]=[C:12]([NH:11][C@H:7]2[CH2:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6]2)[C:17]([C:18]2[N:19]=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 66053N,N-DimethylethylenediamineHCID 58177355HCID 58177355, compound

Product 1

HCID 69811700HCID 69811700, 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, N*1*,N*1*-dimethyl-ethane-1,2-diamine was used to displace the methylsulfone similar to examples above and the de-protection step was similar to step 5, Example 76, to give N*2*-(2-dimethylamino-ethyl)-N*4*-((S)-1-methanesulfonyl-piperidin-3-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine. MS (ES+): 460.

Sources & evidence

ORD record
ord-156c9d98e124461980de0f740804c278
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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