HCID 58248085, compound → HCID 24821746, compound

HRID 2422185Notes

Reaction equation

HRID 2422185 reaction equation
[F:1][C:2]1[C:3]([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:4][CH:5]=[CH:6][CH:7]=1>[Cl-].[Na+].O>[F:1][C:2]1[C:3]([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:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 58248085HCID 58248085, compound

Product 1

HCID 24821746HCID 24821746, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared from (2R)-2-[(5-{[(1S)-1-(3-fluoropyridin-2-yl)ethyl]thio}-2-methoxy[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol using General method D, except that the reaction mixture was heated to 50° C. for 1.5 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 column chromatography (eluent DCM: methanol gradient) followed by preparative HPLC to yield 20 mg of the title compound.

Workup

  1. customAfter complete reaction the reaction mixture
  2. extractionextracted with DCM (three times)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash column chromatography (eluent DCM: methanol gradient)

Sources & evidence

ORD record
ord-1b13d852ac1e464f87353b734bbd5237
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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