1H-Pyrrolo[2,3-B]pyridin-5-ylboronic acid → N-methyl,N-methylsulfonyl(4-morpholino-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanamine

HRID 2262296Notes

Reaction equation

HRID 2262296 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[CH:10]=[C:9]([CH2:11][N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[S:8][C:6]=2[N:7]=1.B(O)(O)[C:25]1[CH:33]=[N:32][C:28]2[NH:29][CH:30]=[CH:31][C:27]=2[CH:26]=1>>[CH3:17][N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH2:11][C:9]1[S:8][C:6]2[N:7]=[C:2]([C:25]3[CH:26]=[C:27]4[CH:31]=[CH:30][NH:29][C:28]4=[N:32][CH:33]=3)[N:3]=[C:4]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 454802571H-Pyrrolo[2,3-B]pyridin-5-ylboronic acidHCID 56834050N-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)-N-methylmethanesulfonamide

Product 1

HCID 59593077N-methyl,N-methylsulfonyl(4-morpholino-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)methanamineYield 6%

Procedure

(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl-n-methyl-N-(methylsulfonyl)methaneamine and 1H-pyrrolo[2,3-b]pyridin-5-yl-5-boronic acid were reacted following General Procedure A to produce 417 in 6.0% yield MS (Q1) 459.2 (M)+

Sources & evidence

ORD record
ord-9d588031dcac42c1bb149c40b5a1a680
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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