4-Aminobenzoic Acid → HCID 20120398, compound

HRID 2234423Notes

Reaction equation

HRID 2234423 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:19])[CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][NH2:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][N:12]([CH3:19])[CH3:11])=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 81531DiisopropylethylamineHCID 104477N,N,2,2-Tetramethylpropane-1,3-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 20120398HCID 20120398, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminobenzoic acid (Aldrich; 4.0 g, 29.17 mmol) in DMF (100 mL) was added N,N,2,2-tetramethyl-1,3-diaminopropane (Aldrich; 5 mL, 31.38 mmol). An immediate solid precipitate formed. DIPEA (15 ml, 86.11 mmol) was added and the resultant suspension stirred HATU (13 g, 34.18 mmol) was added portionwise at such a rate and time interval as to maintain internal reaction temp <30° C.}. The resultant yellow solution was stirred at ambient temperature, overnight.

Workup

  1. customAn immediate solid precipitate formed
  2. additionwas added portionwise at such a rate and time interval as
  3. temperatureto maintain internal reaction temp <30° C.}

Sources & evidence

ORD record
ord-a3fbc3185b07428a970a7d164806fb45
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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