N,N-Dimethylglycine → HCID 58653777, compound

HRID 459041Notes

Reaction equation

HRID 459041 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]([CH3:39])[CH2:35][C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:33][N:34]([CH3:39])[CH2:35][C:36]([O:20][CH2:19][CH: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:37]

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 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-one

Product 1

HCID 58653777HCID 58653777, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

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: 250 mg, 0.57 mMol), N,N-dimethylglycine (150 mg, 1.46 mMol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (300 mg, 1.56 mMol), and 4-dimethylaminopyridine (5 mg, 0.04 mMol) were suspended in 5 ml of DMF at room temperature. The mixture was stirred overnight and then concentrated. The residue was purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane) to give the free base of the title compound as a white solid (250 mg). Mp 185–198° C.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f59543b3072f493187eefbb0d1baa91e
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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