3-Aminobenzoic Acid → 3-{[(5-Fluoro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoic acid

HRID 589745Notes

Reaction equation

HRID 589745 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:16][C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

3

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride2×

Product 1

HCID 569418893-{[(5-Fluoro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoic acidYield 45%

Procedure

The product was prepared according to General Procedure 1, described in Example 1, with 5-fluoro-3-methylbenzothiophene-2-sulfonyl chloride (Intermediate 14) (26 mg, 0.10 mmol) and 3-aminobenzoic acid (26 mg, 0.19 mmol). The title compound was obtained in 45% yield (16.5 mg). MS (ESI+) calcd mass for C16H12FNO4S2 365.019178, found 365.018988.

Workup

  1. customThe product was prepared

Sources & evidence

ORD record
ord-740018a01f134d068d04b74f1a524ef6
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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