Hydrochloric Acid → HCID 57963243, compound

HRID 1187289Notes

Reaction equation

HRID 1187289 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([C:20]2[C:28]3[C:27](Cl)=[N:26][CH:25]=[N:24][C:23]=3[N:22](S(C3C=CC(C)=CC=3)(=O)=O)[CH:21]=2)=[O:19])[C:12]=1[F:40])C1C=CC=CC=1.[OH-:42].[K+].Cl.[CH3:45]O>>[NH2:10][C:11]1[C:12]([F:40])=[C:13]([C:18]([C:20]2[C:28]3[C:27]([O:42][CH3:45])=[N:26][CH:25]=[N:24][C:23]=3[NH:22][CH:21]=2)=[O:19])[C:14]([F:17])=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 58316934HCID 58316934, compound

Product 1

HCID 57963243HCID 57963243, compound

Conditions

Temperature
70 °C

Procedure

{3-[4-Chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-2,4-difluoro-phenyl}-carbamic acid benzyl ester (35, 152 mg, 0.255 mmol) is combined with 15 mL of methanol and potassium hydroxide (1.06 g, 18.9 mmol) is added. The mixture is heated at 70° C. for 36 hours, then 6 N aqueous hydrochloric acid is added and the mixture is extracted with ethyl acetate. The organic layer is washed with brine, then dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (36, 0.03 mg). MS (ESI) [M+H]+=305.1.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is purified by silica gel column chromatography
  8. washeluting with ethyl acetate and hexane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e14bce6ec5e4401a90e4affe99cd1e21
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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