HCID 58248088, compound → HCID 24821814, compound

HRID 2422181Notes

Reaction equation

HRID 2422181 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([S:10][C:11]1[N:12]=[C:13]([NH:22][C@H:23]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][OH:25])[C:14]2[S:19][C:18]([O:20]C)=[N:17][C:15]=2[N:16]=1)[CH3:9]>C(=O)(O)[O-].[Na+].O>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([S:10][C:11]1[N:12]=[C:13]([NH:22][C@@H:23]([CH2:24][OH:25])[CH2:26][CH:27]([CH3:28])[CH3:29])[C:14]2[S:19][C:18](=[O:20])[NH:17][C:15]=2[N:16]=1)[CH3:9]

Participants

4

Reactant 1

HCID 58248088HCID 58248088, compound

Product 1

HCID 24821814HCID 24821814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared starting from (2R)-2-[(5-{[1-(3-fluoropyridin-4-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 2 h. After complete reaction the reaction mixture was diluted with sat. sodium bicarbonate aq. and water (1:1) and extracted with DCM (three times). The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The product was purified by flash column chromatography (eluent heptane:ethyl acetate gradient) to yield the title compound as a mixture of diastereomers (194 mg).

Workup

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

Sources & evidence

ORD record
ord-4d05ba22df0247b595523049f8920e78
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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