(2-Nitrophenoxy)acetic acid → HCID 57663904, compound

HRID 1510256Notes

Reaction equation

HRID 1510256 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.ON1C2N=CC=CC=2N=N1.[N+:48]([C:51]1[CH:61]=[CH:60][CH:59]=[CH:58][C:52]=1[O:53][CH2:54][C:55](O)=[O:56])([O-])=O.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[NH2:48][C:51]1[CH:61]=[CH:60][CH:59]=[CH:58][C:52]=1[O:53][CH2:54][C:55]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1)=[O:56]

Participants

8

Reactant 5

HCID 15883(2-Nitrophenoxy)acetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 15126544-(Pyridin-4-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57663904HCID 57663904, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-pyridinyl)aniline (400 mg), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.34 g), 1-hydroxy-7-azabenzotriazole (480 mg) and (2-nitrophenoxy)acetic acid (695 mg) in N,N-dimethylformamide (10 ml) was added N,N-diisopropylethylamine (1.3 ml), which was stirred overnight at ambient temperature. The reaction mixture was poured into water (30 ml) and stirred for 30 minutes. Insoluble material was collected, washed with water, dried and purified by column chromatography on silica gel (gradient, CHCl3, 10% MeOH in CHCl3). The aliquots of obtained product (100 mg) and 10% palladium on carbon (50% wet, 30 mg) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 3 hours under an atmospheric pressure of hydrogen. The catalyst was removed and evaporated under reduced pressure. The resultant was purified by column chromatography on silica gel (gradient, CHCl3, 10% MeOH in CHCl3), which was recrystallized from EtOH to give 2-(2-aminophenoxy)-N-[4-(4-pyridinyl)phenyl]acetamide (30 mg) as an off-white powder.

Workup

  1. stirringstirred for 30 minutes
  2. customInsoluble material was collected
  3. washwashed with water
  4. customdried
  5. custompurified by column chromatography on silica gel (gradient, CHCl3, 10% MeOH in CHCl3)
  6. stirringThe aliquots of obtained product (100 mg) and 10% palladium on carbon (50% wet, 30 mg) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 3 hours under an atmospheric pressure of hydrogen
  7. customThe catalyst was removed
  8. customevaporated under reduced pressure
  9. customThe resultant was purified by column chromatography on silica gel (gradient, CHCl3, 10% MeOH in CHCl3), which
  10. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-21415cb8b1d54a5e9e5758878d69d448
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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