Pyridine → HCID 56941453, compound

HRID 589720Notes

Reaction equation

HRID 589720 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([O:19]C)=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:24])[C:6]=2[CH:25]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1.[Li+].[OH-]>C(Cl)Cl>[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:24])[C:6]=2[CH:25]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 7918Acetic AnhydrideHCID 66799911HCID 66799911, compound

Product 1

HCID 56941453HCID 56941453, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-{[(5-amino-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (7 mg, 0.019 mmol) in CH2Cl2 (200 uL), acetic anhydride (5 mg, 0.022 mmol) and pyridine (11 uL) was stirred at room temperature over night. The mixture was concentrated and dissolved in THF/water (1 mL) and LiOH (1 mg, 0.024 mmol) was added. The diacetylated intermediate was hydrolyzed at room temperature for 4 h. The crude product was purified by preparative HPLC (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/MeCN) to give 4.3 mg (56%) of the title compound. MS (ESI+) calcd for C18H16N2O5S2 404.050063, found 404.050323.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in THF/water (1 mL)
  3. customThe crude product was purified by preparative HPLC (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/MeCN)

Sources & evidence

ORD record
ord-964571ffc9184388921f258394b02c45
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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