4-Aminobenzoic Acid → HCID 57732251, compound

HRID 1808254Notes

Reaction equation

HRID 1808254 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.C(N(CC)C(C)C)(C)C.[F:49][C:50]([F:60])([F:59])[C:51]1[CH:58]=[CH:57][C:54]([CH2:55][NH2:56])=[CH:53][CH:52]=1>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:56][CH2:55][C:54]2[CH:53]=[CH:52][C:51]([C:50]([F:49])([F:59])[F:60])=[CH:58][CH:57]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 6228DimethylformamideHCID 768044-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57732251HCID 57732251, compound

Procedure

To a mixture of p-aminobenzoic acid (5.0 g, 36 mmol) and HBTU (14 g, 36 mmol) in DMF (50 mL, 600 mmol) at 0° C. were added N,N-diisopropylethylamine (19 mL, 110 mmol) and 4-(trifluoromethyl)benzylamine (6.2 mL, 44 mmol). The reaction mixture was slowly warmed to ambient temperature. The reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were washed successively with water, aqueous lithium chloride, and brine, dried over sodium sulfate, filtered and concentrated in vacuo (8.2 g, 70%).

Workup

  1. customThe reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed successively with water, aqueous lithium chloride, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo (8.2 g, 70%)

Sources & evidence

ORD record
ord-4914d402234a4be4b441975642b210b3
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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