Acetic Acid → HCID 67002774, compound

HRID 2362736Notes

Reaction equation

HRID 2362736 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([OH:32])[CH2:31][CH2:30][NH:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([I:11])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[C:33](O)(=[O:35])[CH3:34].C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([OH:32])[CH2:31][CH2:30][N:29]([C:33](=[O:35])[CH3:34])[CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([I:11])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 67003760HCID 67003760, compound

Product 1

HCID 67002774HCID 67002774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ambient solution of 3-(5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)pyrrolidin-3-ol (Example 117D) (180 mg, 0.300 mmol) in N,N-dimethylformamide (10 mL) was added acetic acid (36 mg, 0.599 mmol), triethylamine (0.125 mL, 0.899 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (137 mg, 0.359 mmol). The reaction was stirred at room temperature for 3 hours and was quenched by the addition of water and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purifed by flash column chromatography on silica gel, eluting with a gradient of 0 to 5% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 643.3 (M+H)+.

Workup

  1. customwas quenched by the addition of water and ethyl acetate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washeluting with a gradient of 0 to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-5459c4258ec84fd8895e6e259f21f9bd
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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