4-Nitrobenzoic Acid → HCID 58481149, compound

HRID 1625720Notes

Reaction equation

HRID 1625720 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:46]([C:49]1[CH:54]=[CH:53][C:52]([CH2:55][CH:56]([NH2:60])[C:57]([OH:59])=[O:58])=[CH:51][C:50]=1[NH2:61])(=[O:48])[CH3:47]>CN(C=O)C>[C:46]([C:49]1[CH:54]=[CH:53][C:52]([CH2:55][CH:56]([NH:60][C:8](=[O:10])[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:57]([OH:59])=[O:58])=[CH:51][C:50]=1[NH2:61])(=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67365667HCID 67365667, compound

Product 1

HCID 58481149HCID 58481149, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 4-nitrobenzoic acid (50.1 mg), HATU (114 mg) and DIEA (105 μL) was added 1 mL DMF and the mixture was stirred for 30 minutes. Then the resulting solution was added to 3-(4-acetyl-3-aminophenyl)-2-aminopropanoic acid (66.7 mg, 1.0 equiv) in 1.0 mL DMF, and the reaction was stirred at room temperature, monitored by LC-MS. The title product was then isolated by preparative HPLC. 1H NMR (400 MHz, MeOD): δ 8.28 (d, J=8.8 Hz, 2H), 7.93 (d, J=8.8 Hz, 2H), 7.72 (d, J=8.4 Hz, 1H), 6.69 (d, J=1.6 Hz, 1H), 6.61 (dd, J′=8.4 Hz, J″=1.6 Hz, 1H), 3.28 (dd, J′=13.8 Hz, J″=10.0 Hz, 1H), 3.02 (dd, J′=13.8 Hz, J″=10.0 Hz, 1H), 2.51 (s, 3H); ESI-MS (m/z) 372.34 (MH+).

Workup

  1. stirringthe reaction was stirred at room temperature

Sources & evidence

ORD record
ord-5601bfbaff994012a5688de83e3104e5
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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