Pyridine → HCID 56941887, compound

HRID 589676Notes

Reaction equation

HRID 589676 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([S:27](Cl)(=[O:29])=[O:28])=[C:24]([CH3:31])[C:23]=2[CH:32]=1>CC#N>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([S:27]([NH:7][C:8]3[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])(=[O:29])=[O:28])=[C:24]([CH3:31])[C:23]=2[CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 56941887HCID 56941887, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine (200 μL, 2.48 mmol) was added to a solution of methyl 3-aminobenzoate (188 mg, 1.24 mmol) and 5-chloro-3-methyl-benzothiophene-2-sulfonyl chloride (349 mg, 1.24 mmol) in MeCN (10 mL). The reaction mixture was stirred at room temperature over night. After removal of the solvents, the residue was dissolved in EtOAc and water. The phases were separated, and the organic solution was washed with 1M HCl twice, water twice and brine then dried (MgSO4). The crude product, obtained after evaporation of the solvents, was crystallized from MeOH (ca 5 mL). The solid product was triturated using heptane, giving the intermediate methyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate as an off-white solid (432 mg, 88%). 1H NMR (500 MHz, CDCl3) δ ppm 2.46 (s, 3 H) 2.45 (s, 3 H) 6.91 (s, 1 H) 7.37 (t, J=7.81 Hz, 1 H) 7.43-7.47 (m, 2 H) 7.72 (d, J=1.96 Hz, 1 H) 7.72 (d, J=8.76 Hz, 1 H) 7.76 (t, J=1.83 Hz, 1 H) 7.85 (dt, J=7.81, 1.34 Hz, 1 H). MS (ESI+) 396 m/z [M+H]+.

Workup

  1. customAfter removal of the solvents
  2. dissolutionthe residue was dissolved in EtOAc
  3. customThe phases were separated
  4. washthe organic solution was washed with 1M HCl twice
  5. dry with materialwater twice and brine then dried (MgSO4)
  6. customThe crude product, obtained
  7. customafter evaporation of the solvents
  8. customwas crystallized from MeOH (ca 5 mL)
  9. customThe solid product was triturated

Sources & evidence

ORD record
ord-4bc85f3762d44a279ee1ac1050d70996
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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