Phthalic Anhydride → 2-({[(3-{[3-{[(5-Chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]amino}carbonyl)benzoic acid

HRID 1892979Notes

Reaction equation

HRID 1892979 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=3)[C:12]([NH:21][S:22]([C:25]3[S:26][C:27]([Cl:30])=[CH:28][CH:29]=3)(=[O:24])=[O:23])=[N:11]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[C:40]1(=[O:50])[O:45][C:43](=[O:44])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12>C1COCC1>[Cl:30][C:27]1[S:26][C:25]([S:22]([NH:21][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:10]([CH2:9][C:5]3[CH:4]=[C:3]([CH2:2][NH:1][C:40]([C:41]4[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=4[C:43]([OH:45])=[O:44])=[O:50])[CH:8]=[CH:7][CH:6]=3)[N:11]=2)(=[O:24])=[O:23])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 59455974HCID 59455974, compound

Product 1

HCID 594561092-({[(3-{[3-{[(5-Chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]amino}carbonyl)benzoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-{[3-(aminomethyl)phenyl]methyl}-4-(methyloxy)-1H-indazol-3-yl]-5-chloro-2-thiophenesulfonamide (for a preparation see Intermediate 4) (0.046 g, 0.1 mmol) in THF (0.5 ml) was added N,N-diisopropylethylamine (0.035 ml, 0.2 mmol), followed by phthalic anhydride (0.014 g, 0.1 mmol). The solution was stirred for 18 hours at room temperature, concentrated in a blow-down unit and the residue was dissolved in DMSO (0.5 ml) and purified by mass directed auto-preparative HPLC (Method E) to give the title compound (35 mg, 51%).

Workup

  1. concentrationconcentrated in a blow-down unit
  2. dissolutionthe residue was dissolved in DMSO (0.5 ml)
  3. custompurified by mass

Sources & evidence

ORD record
ord-5507867dc31b41f7a7258471764d8525
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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