Hydrochloric Acid → 3-(3,5-Dimethyl-4-morpholin-4-ylmethyl-1H-pyrrol-2-ylmethylene)-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one hydrochloride

HRID 44280Notes

Reaction equation

HRID 44280 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][N:19]3[CH2:23][CH2:22][O:21][C:20]3=[O:24])[CH:16]=2)[NH:11][C:10]1=[O:25].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[CH2:32]=O.[ClH:34]>C(O)(=O)C>[ClH:34].[CH3:1][C:2]1[C:6]([CH2:32][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][N:19]3[CH2:23][CH2:22][O:21][C:20]3=[O:24])[CH:16]=2)[NH:11][C:10]1=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 666363323-(3,5-Dimethyl-1H-pyrrol-2-ylmethylene)-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one

Product 1

HCID 666366103-(3,5-Dimethyl-4-morpholin-4-ylmethyl-1H-pyrrol-2-ylmethylene)-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the compound obtained in Step A (1.3 mmoles) in acetic acid (20 ml) there are added at 0° C. morpholine (1.43 mmoles) and formaldehyde (37% aq., 1.3 mmoles). The reaction mixture is stirred overnight at ambient temperature. The mixture is evaporated to dryness and the residue is purified on silica gel (SiO2; gradient 100% DCM to DCM/MeOH 9/1). The product obtained is converted into the hydrochloride as described in Step E of Example 19 to yield the title product. Mixture of Z/E isomers (99.5/0.5)

Workup

  1. customThe mixture is evaporated to dryness
  2. customthe residue is purified on silica gel (SiO2; gradient 100% DCM to DCM/MeOH 9/1)
  3. customThe product obtained

Sources & evidence

ORD record
ord-cec1c9b0695d40d194e5ab50c118d6ad
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

Loading…