Cyanogen Bromide → HCID 49853813, compound

HRID 1400036Notes

Reaction equation

HRID 1400036 reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.C[CH2:25][N:26](C(C)C)C(C)C.N#CBr>CN(C=O)C.O>[C:25]([N:3]1[CH2:4][CH:5]2[C:1]([C:7]3[CH:8]=[CH:9][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:11][CH:12]=3)([CH2:6]2)[CH2:2]1)#[N:26]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 67515007HCID 67515007, compound2×

Product 1

HCID 49853813HCID 49853813, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (0.2 g, 0.57 mmol) in DMF (5 mL) were added DIPEA (0.3 mL, 1.7 mmol) and cyanogen bromide (0.18 g, 1.1 mmol) at r.t. The reaction mixture was stirred at 100° C. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3) to provide the title compound (0.05 g, 26%) as white solid.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3)

Sources & evidence

ORD record
ord-ca2cc7e977a54b739e1f4299374eaf0c
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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