Pyridine → HCID 59677009, compound

HRID 2104456Notes

Reaction equation

HRID 2104456 reaction equation
N1C=CC=CC=1.F.[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.N1C=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 1049PyridineHCID 64774Pyridine, hydrofluoride (1:1)HCID 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 silica gel column chromatography (chloroform:methanol=9:1) to give the title compound (0.31 g).

Workup

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

Sources & evidence

ORD record
ord-453eacef98f044c886ea57d6253ad6b1
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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