Pyridine → HCID 56941887, 화합물

HRID 589676노트

반응식

HRID 589676 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 56941887HCID 56941887, 화합물수율 88%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-4bc85f3762d44a279ee1ac1050d70996
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233946B2

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