1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58758436, compound

HRID 459048Notes

Reaction equation

HRID 459048 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:19]=[C:20]([N:37]2[CH2:41][C@H:40]([CH2:42][N:43]3[CH:47]=[CH:46][N:45]=[N:44]3)[O:39][C:38]2=[O:48])[CH:21]=[CH:22][C:23]=1[C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH2:34][C@@H:33]([CH2:35]O)[O:32][N:31]=2)=[CH:28][CH:29]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:35][C@H:33]1[O:32][N:31]=[C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:23]3[CH:22]=[CH:21][C:20]([N:37]4[CH2:41][C@H:40]([CH2:42][N:43]5[CH:47]=[CH:46][N:45]=[N:44]5)[O:39][C:38]4=[O:48])=[CH:19][C:18]=3[F:17])=[CH:25][N:26]=2)[CH2:34]1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 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 19753820124073-08-1

Product 1

HCID 58758436HCID 58758436, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude carbamate prepared as above (2 g, 8.6 mmol), (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: 1 g, 2.28 mmol), 4-dimethylaminopyridine (0.05 g, 0.4 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.28 g, 6.67 mmol) were combined in DMF (10 ml). The suspension was allowed to stir for 16 hours at room temperature, diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The residue obtained upon filtration and evaporation was purified via chromatography (silica gel, 0.5 to 5% methanol in dichloromethane). Evaporation of the product containing fractions and trituration of the resulting solid with diethyl ether yielded the title compound as an off-white solid (1.28 g), melting point: 121° C.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe residue obtained upon filtration and evaporation
  4. customwas purified via chromatography (silica gel, 0.5 to 5% methanol in dichloromethane)
  5. customEvaporation of the product
  6. additioncontaining fractions and trituration of the resulting solid with diethyl ether

Sources & evidence

ORD record
ord-768c5764ad5d41468a781f251434d2a8
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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