HCID 58248070, compound → HCID 24821815, compound

HRID 2422179Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([S:10][C:11]2[N:12]=[C:13]([NH:22][C@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25])[C:14]3[S:19][C:18]([O:20]C)=[N:17][C:15]=3[N:16]=2)[CH3:9])=[N:6][CH:7]=1>[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([S:10][C:11]2[N:12]=[C:13]([NH:22][C@@H:23]([CH2:24][OH:25])[CH2:26][CH:27]([CH3:28])[CH3:29])[C:14]3[S:19][C:18](=[O:20])[NH:17][C:15]=3[N:16]=2)[CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The title compound was prepared from (2R)-2-[(5-{[(1S)-1-(5-fluoropyridin-2-yl)ethyl]thio}-2-methoxy[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol from the previous step using General method D, except that the reaction mixture was stirred at 50° C. for 3 h. After complete reaction the reaction mixture was diluted with Brine and extracted with DCM (three times). The combined organic extracts were dried over magnesium sulphate and concentrated in vacuo. The product was purified by flash chromatography (eluent DCM: methanol gradient). Further purification by preparative HPLC (column Chiralcel OJ, eluent: ethanol, flow: 8 mL/min) yielded 113 mg of the title compound.

Workup

customAfter complete reaction the reaction mixture
extractionextracted with DCM (three times)
dry with materialThe combined organic extracts were dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe product was purified by flash chromatography (eluent DCM: methanol gradient)
customFurther purification by preparative HPLC (column Chiralcel OJ, eluent: ethanol, flow: 8 mL/min)

Sources & evidence

ORD record: ord-6614099ff6a44c72a4a9949d4f6b0320
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960395B2

Reaction notes

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