2-Hydroxyisobutyric acid → HCID 86618372, compound

HRID 2098624Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1.[OH:24][C:25]([CH3:30])([CH3:29])[C:26](O)=O>>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11]3[CH:12]=[C:13]([NH:17][CH2:26][C:25]([OH:24])([CH3:30])[CH3:29])[CH:14]=[CH:15][CH:16]=3)=[CH:8][C:6]=2[N:7]=1

Participants

Reactant 2

HCID 116712-Hydroxyisobutyric acid

HCID 59593132HCID 59593132, compound

Product 1

HCID 86618372HCID 86618372, compound

Procedure

3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)benzenamine (50 mg) was reacted with 2-hydroxyisobutyric acid via General Procedure I to give N-(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-hydroxy-2-methylpropanamine. 62 mg of the crude N-(3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-hydroxy-2-methylpropanamine was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A. The product was purified by reverse phase HPLC to yield 16.2 mg of 112. MS (Q1) 515 (M)+.

Sources & evidence

ORD record: ord-d6413971d498408982e5d12d63d1f188
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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