Hydrochloric Acid → HCID 57963246, compound

HRID 1690021Notes

Reaction equation

HRID 1690021 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[CH:27]=[N:26][CH:25]=[N:24][C:23]=3[NH:22][CH:21]=2)=[O:19])[C:12]=1[F:29])C1C=CC=CC=1.COC(=O)NC1C=CC(F)=C(C(C2C3C=NC=NC=3NC=2)=O)C=1F.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH2:10][C:11]1[C:12]([F:29])=[C:13]([C:18]([C:20]2[C:28]3[CH:27]=[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 66901712HCID 66901712, compoundHCID 66901737HCID 66901737, compound

Product 1

HCID 57963246HCID 57963246, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of [2,4-difluoro-3-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-carbamic acid benzyl ester (25) and [2,4-difluoro-3-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-carbamic acid methyl ester (26) from the last step was dissolved in 30 mL of 1,4-dioxane and 25 mL of 10 N aqueous sodium hydroxide was added. The mixture was heated to reflux for 2 hours, then acidified with 6 N hydrochloric acid and adjusted to pH˜8 with addition of some sodium bicarbonate. This was extracted with ethyl acetate and the organic layer was washed with water and brine, then dried with magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the resulting residue was suspended in acetonitrile and sonicated for 30 minutes. The precipitated material was collected by filtration to provide the desired compound as a yellow solid (27, 263 mg). 1H-NMR(dmso-d6) was consistent with the desired compound. MS(ESI) [M+H+]=274.8.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionThis was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum
  8. customsonicated for 30 minutes
  9. filtrationThe precipitated material was collected by filtration

Sources & evidence

ORD record
ord-3f720abef7d946549650973de3397d3f
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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