O-Phenylenediamine → HCID 86602076, compound

HRID 724641Notes

Reaction equation

HRID 724641 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:10]([NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:31])[CH:25]=2)=[CH:20][CH:19]=1)[C:14](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:72]1([NH2:79])[C:73]([NH2:78])=[CH:74][CH:75]=[CH:76][CH:77]=1>CN(C)C=O>[NH2:78][C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][C:72]=1[NH:79][C:14](=[O:15])[CH:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:28](=[O:29])(=[O:30])[NH:27][C:26](=[O:31])[CH:25]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58746762HCID 58746762, compound

Product 1

HCID 86602076HCID 86602076, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-2-((2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoylamino)-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-propanoic acid (15.0 mg, 0.0276 mmol) in N,N-dimethylformamide (3 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (10.5 mg, 0.027 mmol) and N,N-diisopropylethylamine (24 μL, 0.14 mmol) and premixed for 5 minutes. To the solution was added 1,2-benzenediamine (4.2 mg, 0.04 mmol) and stirred at room temperature overnight. Preformed ester was yellow in color and upon addition of the diamine continued to darken over several minutes. Product was purified by preparative LCMS to afford the desired product (7.3 mg, 42%). LCMS found for C32H36N5O7S (M+H)+: m/z=634.2.

Workup

  1. additionpremixed for 5 minutes
  2. waitto darken over several minutes
  3. customProduct was purified by preparative LCMS

Sources & evidence

ORD record
ord-ac385aee039c46e28fd269be515f450f
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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