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Ethanol → HCID 23130529, compound

HRID 2079969
Notes
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Reaction equation

HRID 2079969 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:2]1[N:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 231304292-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 23130529HCID 23130529, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst
HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

2-Amino-5-nitro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (74 mg, 0.20 mmol) described in Preparation Example A+-9, an iron powder (56 mg, 1.0 mmol) and ammonium chloride (21 mg, 0.40 mmol) were suspended in a solvent mixture of ethanol (2 mL) and water (0.5 mL), the solution was stirred at 60° C. for 3 hours, then, it was stirred at 90° C. for 6 hours. The reaction solution was cooled to room temperature, then, it was filtered through Celite pad. The filtrate was evaporated in vacuo, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water:mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (54.4 mg) was obtained as a trifluoroacetic acid salt.

Workup

  1. stirringit was stirred at 90° C. for 6 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationit was filtered through Celite pad
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water:mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-c688d761f13644d4bce8b0ae6496e5ee
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes