Реакция #1973977

ord-27feb9f7feb0422ab42d3f31535699c2

Уравнение реакции

COc1c(-c2ccc3nc(N)sc3c2)cc(-n2ccc(=O)[nH]c2=O)cc1C(C)(C)C
product
COc1c(-c2ccc3nc(N)sc3c2)cc(-n2ccc(=O)[nH]c2=O)cc1C(C)(C)C
1-(3-(2-aminobenzo[d]thiazol-6-yl)-5-tert-butyl-4-methoxy-phenyl)pyrimidine-2,4(1H,3H)-dione
CS(=O)(=O)Cl
methanesulfonyl chloride
c1ccncc1
pyridine
COc1c(-c2ccc3nc(NS(C)(=O)=O)sc3c2)cc(-n2ccc(=O)[nH]c2=O)cc1C(C)(C)C
title compound
Выход 4.6%
COc1c(-c2ccc3nc(NS(C)(=O)=O)sc3c2)cc(-n2ccc(=O)[nH]c2=O)cc1C(C)(C)C
N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)benzo[d]thiazol-2-yl)methanesulfonamide
Выход 4.6%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Концентрированиеconcentrated in vacuo
  2. 2
    ДругоеThe crude product was purified by C-18 reverse-phase

Методика

To a solution of the product from Example 53 (0.35 g, 0.83 mmol) in anhydrous CH2Cl2 (50 mL) was added methanesulfonyl chloride (194 μL, 2.49 mmol) and pyridine (1.34 mL, 16.6 mmol). The resulting mixture was stirred at room temperature for 16 h and concentrated in vacuo. The crude product was purified by C-18 reverse-phase HPLC using an acetonitrile:H2O (0.1% TFA) gradient to give the title compound (19 mg, 4%). 1H NMR (300 MHz, DMSO-d6) δ 13.09 (s, 1 H) 11.41 (d, J=1.84 Hz, 1 H) 7.96 (d, J=1.47 Hz, 1 H) 7.77 (d, J=8.09 Hz, 1 H) 7.57 (dd, 1 H) 7.42 (d, J=8.09 Hz, 1 H) 7.25-7.32 (m, 2 H) 5.64 (dd, J=8.09, 2.21 Hz, 1 H) 3.25 (s, 3 H) 3.02 (s, 3 H) 1.40 (s, 9 H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08501238B2uspto-grants-2013_08