Dimethylformamide → HCID 86609333, compound

HRID 459038Notes

Reaction equation

HRID 459038 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.[CH3:33][N:34]([CH3:42])[CH:35]([CH3:41])[CH2:36][CH2:37][C:38](O)=[O:39].Cl.C(N=C=NCCCN(C)C)C.CN(C=O)C>CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:33][N:34]([CH3:42])[CH:35]([CH3:41])[CH2:36][CH2:37][C:38]([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:39]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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-oneHCID 18442969HCID 18442969, compound

Product 1

HCID 86609333HCID 86609333, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(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 (Example 1,150 mg, 0.342 mmol), 4-(dimethylamino)pentanoic acid (63.6 mg, 0.514 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (131.5 mg, 0.69 mmol), and 4-dimethylaminopyridine (10.5 mg, 0.09 mmol) were added to DMF (3 ml). The reaction was allowed to stir overnight at room temperature followed by addition to EtOAc (40 ml). The precipitate was collected by filtration and then purified by column chromatography 0–5% MeOH/CH2Cl2 to yield a white powder (100 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. custompurified by column chromatography 0–5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6235b2e32e484934acb1eb3fcf835fa7
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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