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Water → HCID 58474538, compound

HRID 1400865
Notes
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Reaction equation

HRID 1400865 reaction equation
[C:1]([O:4][CH2:5][C:6]([N:8]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][C:31]=3[F:39])[CH:21]=2)=[N:16][CH:15]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])(=[O:3])[CH3:2].[Cl-].[NH4+].O>C(O)C.[Fe]>[C:1]([O:4][CH2:5][C:6]([N:8]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:31]=3[F:39])[CH:21]=2)=[N:16][CH:15]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58474731HCID 58474731, compound

Product 1

HCID 58474538HCID 58474538, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702
Ethanol
Solvent

Procedure

The reaction mixture consisting of 206 (300 mg, 0.538 mmol), ammonium chloride (24.75 mg, 0.463 mmol) and iron powder (255 mg, 4.57 mmol) in ethanol (6 mL)/water (3.0 mL) was heated to reflux for 1 h. The reaction mixture was filtered while hot and concentrated. The residue was purified by Biotage (MeOH/DCM, 0-20%, SNAP 25 g cartridge) to give the title compound 207 (133 mg, 0.252 mmol, 47% yield) as a white solid. MS: 528 (MH)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. filtrationThe reaction mixture was filtered while hot and
  4. concentrationconcentrated
  5. customThe residue was purified by Biotage (MeOH/DCM, 0-20%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-99bdc19d750142ecbdf07521207de230
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906852B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes