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Pyridine → HCID 18969790, compound

HRID 399075
Notes
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Reaction equation

HRID 399075 reaction equation
[CH3:1][C:2]1([CH3:23])[CH:5]([OH:6])[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.N1C=CC=CC=1.[CH3:30][C:31](OC(C)=O)=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O.O>[CH3:1][C:2]1([CH3:23])[CH:5]([O:6][C:31](=[O:32])[CH3:30])[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:3]1[C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18969768HCID 18969768, compound

Product 1

HCID 18969790HCID 18969790, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 62 (150 mg) in CH2Cl2 (3 mL) at r.t., was added pyridine (370 mL), Ac2O (215 μL) and DMAP (5 mg). The mixture was stirred at r.t. for 2 hr and diluted with EtOAc and H2O. The organic phase was washed with HCl 1N, brine, dried (MgSO4) and the solvents evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30)) to give the title compound as a white solid, m.p. 60°-61° C.

Workup

  1. washThe organic phase was washed with HCl 1N, brine
  2. dry with materialdried (MgSO4)
  3. customthe solvents evaporated
  4. customThe residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30))

Sources & evidence

ORD record
ord-41a3ca67a7ba40559bb09c013b5fd1dc
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817700

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes