Pyridine → HCID 67069936, compound

HRID 2390815Notes

Reaction equation

HRID 2390815 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[C:9](=[O:14])[NH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][C:3]=1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=1.N1C=CC=C[CH:33]=1.[C:38](OC(=O)C)(=[O:40])[CH3:39]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:15]([C:5]1[CH:6]=[C:7]([C:8]2[C:9]([O:14][CH3:33])=[N:10][CH:11]=[CH:12][CH:13]=2)[C:2]([NH:1][C:38](=[O:40])[CH3:39])=[C:3]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)[CH:4]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67069927HCID 67069927, compound

Product 1

HCID 67069936HCID 67069936, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

step 6—To solution of 88 (0.087 g, 0.19 mmol) in DCM (5 mL) at 0° C. was added pyridine (23 □L) and followed by acetic anhydride (0.02 mL, 0.23 mmol). The reaction was allowed to warm to RT and stirred overnight then diluted with DCM and saturated aqueous NaHCO3. The aqueous layer was separated and extracted with DCM. The combined extract was washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC plate developed with 40% EtOAc/hexanes to afford 0.045 g (46%) of N-[4-tert-butyl-2-[2-(4-methanesulfonylamino-phenyl)-ethyl]-6-(2-methoxy-pyridin-3-yl)-phenyl]-acetamide (90) as an off-white solid.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with DCM
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified on a preparative SiO2 TLC plate

Sources & evidence

ORD record
ord-aa40ba0a788d455ca3832a954184d613
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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