Dimethylamine → HCID 50995153, compound

HRID 1916128Notes

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]([CH3:21])(=[O:20])=[O:19])[CH2:13]2)[C:8]([C:22]2[N:23]=[C:24]3[C:30]([C:31]#[N:32])=[CH:29][N:28](COCC[Si](C)(C)C)[C:25]3=[N:26][CH:27]=2)=[CH:7][N:6]=1)(=O)=O.O1CCOCC1.[CH3:47][NH:48][CH3:49].CS(C)(=O)=O>>[CH3:47][N:48]([CH3:49])[C:5]1[N:10]=[C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([S:18]([CH3:21])(=[O:19])=[O:20])[CH2:13]2)[C:8]([C:22]2[N:23]=[C:24]3[C:30]([C:31]#[N:32])=[CH:29][NH:28][C:25]3=[N:26][CH:27]=2)=[CH:7][N:6]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 6213Dimethyl Sulfone

HCID 69811302HCID 69811302, compound

Product 1

HCID 50995153HCID 50995153, compound

Procedure

In a dioxane 2-[2-methanesulfonyl-4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-pyrimidin-5-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile derived from step 2 above, dimethylamine was used to displace the methylsulfone similar to examples above and the de-protection step was similar to Scheme 1, step 5 to give 2-[2-dimethylamino-4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-pyrimidin-5-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile. MS: (ES+): 442.

Sources & evidence

ORD record: ord-33459489c5d94790beb5fb56614e70ce
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618103B2

Reaction notes

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