Dimethylamine → HCID 58177237, compound

HRID 1916123Notes

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.[CH3:42][NH:43][CH3:44].CS(C)(=O)=O>>[CH3:42][N:43]([CH3:44])[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]([CH3:23])[CH3:24])(=[O:19])=[O:20])[CH2:13]2)[C:8]([C:25]2[N:26]=[C:27]3[CH:33]=[CH:32][NH:31][C:28]3=[N:29][CH:30]=2)=[CH:7][N:6]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 6213Dimethyl Sulfone

HCID 69815196HCID 69815196, compound

Product 1

HCID 58177237HCID 58177237, compound

Procedure

From {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 derived from Example 3, step 1, dimethylamine 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 N*2*,N*2*-dimethyl-N*4*-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine. MS (ES+): 459.

Sources & evidence

ORD record: ord-7b4eedd612384b00b573eafd23ce11bf
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618103B2

Reaction notes

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