Hydrochloric Acid → 3-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-sulfonylamino]-benzoic Acid

HRID 25320

Reaction equation

HRID 25320 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[NH:26][C:27]4[CH:37]=[CH:36][C:35]5[C:30](=[C:31]([OH:42])[CH:32]=[C:33]([S:38](Cl)(=[O:40])=[O:39])[CH:34]=5)[C:28]=4[N:29]=3)[CH:20]=2)[CH:15]=[CH:16][C:17]=1[CH3:18].Cl>C1COCC1.O>[CH3:11][C:12]1[CH:13]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[NH:26][C:27]4[CH:37]=[CH:36][C:35]5[C:30](=[C:31]([OH:42])[CH:32]=[C:33]([S:38]([NH:1][C:2]6[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=6)[C:5]([OH:7])=[O:6])(=[O:40])=[O:39])[CH:34]=5)[C:28]=4[N:29]=3)[CH:20]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 225666742-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxyl-3H-naphtho[1,2-d]imidazole-7-sulfonyl chloride

Product 1

HCID 225665783-[2-(3',4'-dimethylbiphenyl-3-yl)-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-sulfonylamino]-benzoic AcidYield 4.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an agitated suspension of 3-aminobenzoic acid (0.028 g, 0.2 mmol) in THF (1 mL) was added 2-(3′,4′-dimethylbiphenyl-3-yl)-9-hydroxyl-3H-naphtho[1,2-d]imidazole-7-sulfonyl chloride (0.083 g, 0.18 mmol) and sodium hydroxy (0.018 g, 0.4 mmol) in water (0.5 mL). After agitated for 30 minutes, the reaction mixture was added 6N hydrochloride (2 ml) and concentrated under reduced pressure. The residue was subjected to HPLC (ODS-A, gradient 10-90% CH3CN/water 0.1% TFA) to provide the title compound (0.005 g, 4%) MS(ES) m/z 564 [M+H].

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a5c08e5f3444db3941ed7195666aea4
Source dataset
uspto-grants-2005_02
Patent number
US06858630B2

Linked notes

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