Sodium Bicarbonate → HCID 58777633, compound

HRID 1435322Notes

Reaction equation

HRID 1435322 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16]C)=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:25][CH2:26]2)[N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 6918852RO-4584820

Product 1

HCID 58777633HCID 58777633, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7 °C

Procedure

A suspension of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (200 mg, 0.45 mmol, Example 105) in methylene chloride (40 mL) was treated at 0-5° C. with aluminum chloride (620 mg, 4.7 mmol). The solution was stirred at ˜7° C. for 2.5 hours and treated with ice water (20 mL). The mixture was treated with 10% NaHCO3 (15 mL) and extracted with a mixture of tetrahydrofuran and methylene chloride (2×), dried (Na2SO4), and filtered. Removal of solvent gave an oil that crystallized upon trituration with methylene chloride. This crude solid was purified by silica gel chromatography (5-10% methanol/methylene chloride to give [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-hydroxy-phenyl)-methanone as a white solid (75 mg, 39%) after solvent removal. HRMS, observed: 428.1203; Calcd for (M+H)+: 428.1199

Workup

  1. extractionextracted with a mixture of tetrahydrofuran and methylene chloride (2×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customRemoval of solvent
  5. customgave an oil that
  6. customcrystallized upon trituration with methylene chloride
  7. customThis crude solid was purified by silica gel chromatography (5-10% methanol/methylene chloride

Sources & evidence

ORD record
ord-1db6eb7eb23849baa8e6f50174ef3121
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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