(3-{[(Methanesulfonyl)amino]methyl}phenyl)boronic acid → HCID 86630071, compound

HRID 1365804Notes

Reaction equation

HRID 1365804 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9](I)[S:8][C:6]=2[N:7]=1.[CH3:18][S:19]([NH:22][CH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:21])=[O:20]>>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9]([C:28]3[CH:29]=[C:24]([CH2:23][NH:22][S:19]([CH3:18])(=[O:20])=[O:21])[CH:25]=[CH:26][CH:27]=3)[S:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 22309453(3-{[(Methanesulfonyl)amino]methyl}phenyl)boronic acidHCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 86630071HCID 86630071, compound

Procedure

4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18 was reacted with 3-((methylsulfonylamino)methyl)phenylboronic acid via General Procedure A to give crude (3-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)phenyl)-N-methylsulfonylmethanamine, which was then reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A again to give 126 after purification by reverse HPLC. MS (Q1) 499 (M+)

Sources & evidence

ORD record
ord-530089426bb4430ab07a0e3a6f870034
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

Loading…