Pyridine → HCID 59677009, compound

HRID 902902Notes

Reaction equation

HRID 902902 reaction equation
F.N1C=CC=CC=1.[Si]([O:25][CH2:26][C@@H:27]([NH:48][C:49]([C:51]1[S:52][C:53]2[CH2:54][N:55]([CH3:60])[CH2:56][CH2:57][C:58]=2[N:59]=1)=[O:50])[C@H:28]([NH:35][C:36]([C:38]1[NH:39][C:40]2[C:45]([CH:46]=1)=[CH:44][C:43]([Cl:47])=[CH:42][CH:41]=2)=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1>[Cl:47][C:43]1[CH:44]=[C:45]2[C:40](=[CH:41][CH:42]=1)[NH:39][C:38]([C:36]([NH:35][C@@H:28]([C@H:27]([NH:48][C:49]([C:51]1[S:52][C:53]3[CH2:54][N:55]([CH3:60])[CH2:56][CH2:57][C:58]=3[N:59]=1)=[O:50])[CH2:26][OH:25])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:37])=[CH:46]2

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 14917Hydrofluoric AcidHCID 59676786HCID 59676786, compound

Product 1

HCID 59677009HCID 59677009, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After hydrogen fluoride.pyridine (0.4 ml) was added dropwise to a mixture sulution composed of the compound (0.54 g) obtained in Example 175, pyridine (4.0 ml) and tetrahydrofuran (10 ml) under ice cooling, the reaction mixture was stirred for 18 hours while the temperature thereof was gradually raised to room temperature. The reaction mixture was concentrated, and the resultant residue was purified by column chromatography on silica gel (chloroform:methanol=9:1) to obtain the title compound (0.31 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resultant residue was purified by column chromatography on silica gel (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-1bb48f3d0d92443287f9df902e999d6e
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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