Pyridine → HCID 58758416, compound

HRID 459033Notes

Reaction equation

HRID 459033 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][OH:20])[O:16][N:15]=2)=[CH:12][CH:13]=1.N1C=CC=C[CH:34]=1.[C:39]1(=[O:46])[O:45][C:43](=[O:44])[CH2:42][CH2:41][CH2:40]1>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:43]([O:20][CH2:19][C@H:17]1[O:16][N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:21]4[CH2:25][C@H:24]([CH2:26][N:27]5[CH:31]=[CH:30][N:29]=[N:28]5)[O:23][C:22]4=[O:32])=[CH:3][C:2]=3[F:1])=[CH:9][N:10]=2)[CH2:18]1)(=[O:44])[CH2:42][CH2:41][CH2:40][C:39]([O:45][CH3:34])=[O:46]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7940Glutaric anhydrideHCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Product 1

HCID 58758416HCID 58758416, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydro-3-isoxazolyl]-3-pyridinyl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1, 60 mg, 0.13 mmol) was suspended in 2 mL of anhydrous dimethylformamide. Anhydrous pyridine (1 mL, 12 mmol), 4-dimethylaminopyridine (DMAP) (10 mg, 0.08 mmol) and glutaric anhydride (75 mg, 0.55 mmol) were added and the solution was stirred for 16 hours at room temperature during which the mixture became a clear solution. The reaction was quenched with 1 mL of methanol and purged with diazomethane generated from 1-methyl-3-nitro-1-nitrosoguanidine (MNNG) in a diazomethane generator (Aldrich, cat. No. Z41,173–6) until all product was converted into its methylester as judged by LCMS and the solution turned yellow. The solvent was removed and the product purified by chromatography on silica using a gradient from 0–10% methanol in dichloromethane that yielded 31 mg (40%) of the title compound as a white solid.

Workup

  1. customThe reaction was quenched with 1 mL of methanol
  2. custompurged with diazomethane
  3. customThe solvent was removed
  4. customthe product purified by chromatography on silica using a gradient from 0–10% methanol in dichloromethane that

Sources & evidence

ORD record
ord-87d6045b1c064e77b3c2ede1697a37a1
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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