Hydrochloric Acid → HCID 57963318, compound

HRID 1690038Notes

Reaction equation

HRID 1690038 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:11][C:12]1[C:17]([CH:18]=[O:19])=[C:16]([F:20])[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23].[OH-].[K+].Cl.[C:31](OCC)(=[O:33])C>CO>[F:11][C:12]1[C:17]([CH:18]([OH:19])[C:10]2[C:3]3[C:2]([O:33][CH3:31])=[N:7][CH:6]=[N:5][C:4]=3[NH:8][CH:9]=2)=[C:16]([F:20])[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

Product 1

HCID 57963318HCID 57963318, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 0.200 g, 1.30 mmol) and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (9, 0.401 g, 1.52 mmol), 3.83 mL of methanol was added and this suspension was allowed to stir for 10 minutes, followed by the addition of potassium hydroxide (0.238 g, 4.24 mmol). The reaction was allowed to stir at room temperature over the weekend. The reaction was poured into 25 mL of 1N hydrochloric acid and 25 mL of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel column chromatography eluting with a gradient of 20-100% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-0057, 176 mg). 1N NMR was consistent with the compound structure. MS(ESI) [M+H+]−=413.1.

Workup

  1. stirringto stir at room temperature over the weekend
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washeluting with a gradient of 20-100% ethyl acetate in hexanes
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a94bcca569ac48b0a56d596215a3778a
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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