Hydrochloric Acid → HCID 67003682, compound

HRID 2362653Notes

Reaction equation

HRID 2362653 reaction equation
[Cl:1][C:2]1[C:3]([C:36]2[S:40][C:39]([C:41]3([O:45]COC)[CH2:44][CH2:43][CH2:42]3)=[N:38][CH:37]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][CH:21]([F:24])[CH2:20][CH2:19]4)=[C:13]([F:25])[CH:12]=3)[N:8]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1.Cl>CO>[Cl:1][C:2]1[C:3]([C:36]2[S:40][C:39]([C:41]3([OH:45])[CH2:44][CH2:43][CH2:42]3)=[N:38][CH:37]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][CH:21]([F:24])[CH2:20][CH2:19]4)=[C:13]([F:25])[CH:12]=3)[N:8]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=3)(=[O:28])=[O:27])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67003736HCID 67003736, compound

Product 1

HCID 67003682HCID 67003682, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A 4 mL reaction vial was charged with 5-(5-chloro-2-(3-fluoro-4-((4-fluoropiperidin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 30B) (60.6 mg, 0.085 mmol), methanol (1.0 mL) and 2 normal aqueous hydrochloric acid solution (0.200 ml, 0.658 mmol). The mixture was heated to 60° C. for about 2 hours, and then to 40° C. overnight. The reaction was cooled to room temperature, and the solvent removed under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×1 mL). The combined organics were concentrated to give the title compound, which was used without further purification. MS APCI(+) m/z 669.33 [M+H]+.

Workup

  1. customA 4 mL reaction
  2. customto 40° C.
  3. customovernight
  4. temperatureThe reaction was cooled to room temperature
  5. customthe solvent removed under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (2×1 mL)
  9. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-5216bebe933f4d8fa709e82b8a9e5844
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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