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Hydrochloric Acid → 2-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide

HRID 1187307
Notes
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Reaction equation

HRID 1187307 reaction equation
[CH3:1][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][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23].[OH-].[K+].Cl>CO>[F:11][C:12]1[C:17]([CH:18]([OH:19])[C:10]2[C:3]3[C:2]([CH3:1])=[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][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 513419594-Methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 583169302-Methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide

Product 1

HCID 583169882-methyl-propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide
Yield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask, 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (7, 97.0 mg, 0.728 mmol) is combined with 2-methyl-propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (62, 202 mg, 0.728 mmol), potassium hydroxide (204 mg, 3.64 mmol) and 1.4 mL of methanol. The reaction is stirred at room temperature for 7 hours. The reaction is neutralized with 0.1 N aqueous hydrochloric acid and extracted 3× with ethyl acetate. The combined organic layer is washed with brine, dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (77, 113 mg). MS (ESI) [M−H+]−=409.2.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88dcf1f4e47e4faca2bafb798cad3d77
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673928B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes