Hydroxylamine → HCID 66934280, compound

HRID 881325Notes

Reaction equation

HRID 881325 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15](S(C)(=O)=O)[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.F[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][N:30]=1.NO>CN(C=O)C>[O:25]1[CH2:26][CH2:27][N:22]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([NH:22][CH2:23][CH2:24][OH:25])=[N:30][CH:31]=3)[N:3]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 236508374-(2-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 66934280HCID 66934280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-((4-methanesulfonylpiperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidine (100 mg) was reacted with 2-fluoropyridine-5-boronic acid following General Procedure A. One half of the crude material was heated in the microwave with excess hydroxylamine in DMF to give 188 after reversed phase HPLC purification. MS (Q1) 534 (M)+.

Sources & evidence

ORD record
ord-a50fb5352aa04e119119fd03fa4a3d43
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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