3-Methylsulfonylaminophenylboronic acid → HCID 86630072, compound

HRID 1365800Notes

Reaction equation

HRID 1365800 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][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=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:27]3[CH:28]=[C:23]([NH:22][S:19]([CH3:18])(=[O:20])=[O:21])[CH:24]=[CH:25][CH:26]=3)[S:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 86630072HCID 86630072, compound

Procedure

4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18 was reacted with 3-(methylsulfonylamino)phenylboronic acid via General Procedure A to give crude 3-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)-N-methylsulfonylbenzenamine, 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 121 after purification by reverse HPLC. MS (Q1) 485 (M+)

Sources & evidence

ORD record
ord-cb4c3c5c44714a30b1df5f98e6bf440e
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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