Dimethyl Sulfone → HCID 69813333, compound

HRID 1916153Notes

Reaction equation

HRID 1916153 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]([CH3:46])[C@@H:41]1[CH2:45][CH2:44][NH:43][CH2:42]1.CS(C)(=O)=O>>[CH3:39][N:40]([CH3:46])[C@@H:41]1[CH2:45][CH2:44][N:43]([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)[CH2:42]1

Participants

4

Reactant 3

HCID 6213Dimethyl SulfoneHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 58177355HCID 58177355, compound

Product 1

HCID 69813333HCID 69813333, compound

Procedure

A 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, dimethyl-(R)-pyrrolidin-3-yl-amine 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-((R)-3-dimethylamino-pyrrolidin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine. MS (ES+): 486.

Sources & evidence

ORD record
ord-328473bfa3ce4f388980118467150dc0
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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