Pyridine → HCID 67287059, compound

HRID 2390846Notes

Reaction equation

HRID 2390846 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:12]=2[O:22][CH3:23])[CH:6]=[CH:5][C:4]=1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[Br:17][C:15]1[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:12]([O:22][CH3:23])=[C:11](/[CH:10]=[CH:9]/[C:7]2[CH:6]=[CH:5][C:4]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[C:3]([CH:8]=2)[CH2:2][NH:1][C:35](=[O:37])[CH3:36])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 67287202HCID 67287202, compound

Product 1

HCID 67287059HCID 67287059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

step 2—To a solution of 210 (0.150 g, 0.321 mmol), pyridine (100 L) and DCM (10 mL) cooled to 0° C. was added acetic anhydride (70 μL). The reaction mixture was allowed to warm to RT and stirred overnight. The reaction mixture was diluted with DCM, washed with sat'd. CuSO4 and twice with 1N HCl, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (50 to 75% EtOAc) to afford 45 mg of N-{5-[(E)-2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-vinyl]-2-methanesulfonylamino-benzyl}-acetamide (212).

Workup

  1. washwashed with sat'd
  2. dry with materialCuSO4 and twice with 1N HCl, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with a EtOAc/hexane gradient (50 to 75% EtOAc)

Sources & evidence

ORD record
ord-e8fc4735f50f40689ad57ea17e629610
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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