Hydrochloric Acid → HCID 67003374, compound

HRID 2362625Notes

Reaction equation

HRID 2362625 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31]COC)[CH2:30][CH2:29][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.O1CCCC1.Cl>CO>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([OH:31])[CH2:30][CH2:29][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:16]=[CH:17][C:18]([CH3:19])=[CH:20][CH:21]=3)(=[O:13])=[O:14])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67003444HCID 67003444, compound

Product 1

HCID 67003374HCID 67003374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-(5-chloro-2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1F) (1.5 g, 2.381 mmol) in a solvent mixture of tetrahydrofuran (24 mL) and methanol (10 mL) was added 10% aqueous HCl solution (7.24 ml, 23.81 mmol). The reaction was heated to 65° C. for 8 hours and was then cooled to room temperature. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was extracted with additional ethyl acetate (2×50 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 586.2 [M+H]+.

Workup

  1. temperaturewas then cooled to room temperature
  2. customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with additional ethyl acetate (2×50 mL)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e88ed274eca245ffbc447dc5ec71e580
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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