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2-Nitro-5-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,3-triazol-4-yl)phenyl]thiophene-3-carboxamide → 2-Amino-5-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,3-triazol-4-yl)phenyl]thiophene-3-carboxamide

HRID 385749
Notes
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Reaction equation

HRID 385749 reaction equation
[N+:1]([C:4]1[S:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=3)=[CH:14][CH:13]=2)=[CH:7][C:8]=1[C:9]([NH2:11])=[O:10])([O-])=O>CO.CN(C=O)C.[Pt]>[NH2:1][C:4]1[S:5][C:6]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=3)=[CH:14][CH:13]=2)=[CH:7][C:8]=1[C:9]([NH2:11])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 595258022-Nitro-5-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,3-triazol-4-yl)phenyl]thiophene-3-carboxamide

Product 1

HCID 595259182-Amino-5-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,3-triazol-4-yl)phenyl]thiophene-3-carboxamide

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×
HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 2-nitro-5-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,3-triazol-4-yl)phenyl]thiophene-3-carboxamide (440 mg, 0.99 mmol) in MeOH (15 mL) was added 3% Pt/C doped with 0.6% V (64 mg, 9.9 μmmol). The reaction was stirred under a hydrogen balloon at room temperature overnight. The solution was diluted with MeOH and DMF, filtered through Celite, and evaporated. The crude was triturated with MeOH and filtered to isolate the title compound as a gray solid. The mother liquor was concentrated, triturated with CH2Cl2, and filtered to isolate additional product.

Workup

  1. filtrationfiltered through Celite
  2. customevaporated
  3. customThe crude was triturated with MeOH
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e6d1739226a84e3285ec5727a65dc69b
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367706B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes