Water → HCID 178521526, compound

HRID 545115Notes

Reaction equation

HRID 545115 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([S:8][CH2:9][C:10]([NH:12][CH2:13][C@@H:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=3)[CH2:15]2)=[O:11])[S:6][CH:7]=1)#[N:2].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][N:16]1[CH2:17][CH2:18][O:19][C@@H:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][S:8][C:5]2[S:6][CH:7]=[C:3]([C:1]3[NH:31][N:30]=[N:29][N:2]=3)[N:4]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67169094HCID 67169094, compound

Product 1

HCID 178521526HCID 178521526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resultant product (457 mg) of (22-1), sodium azide (78 mg) and ammonium chloride (525 mg) were suspended in dimethylformamide (3 mL), and the mixture was heated under reflux for 4 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (193 mg) as an orange powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography
  8. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-328d6b93ebeb4608a37f0900c2c04c6f
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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