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HRID2361366

反应详情

EQUATION

反应方程式

HRID 2361366 的结构方程式

REACTANTS

反应物

2
反应SMILES：CC(=O)c1ccc2c(c1)[nH]c1c(C(N)=O)ncc(-c3cccc(-n4cnc5ccccc5c4=O)c3C)c12
HCID67994564

未命名化合物

反应SMILES：C[Mg]Br
HCID178418573

未命名化合物

2 次

PRODUCTS

产物

1
反应SMILES：Cc1c(-c2cnc(C(N)=O)c3[nH]c4cc(C(C)(C)O)ccc4c23)cccc1-n1cnc2ccccc2c1=O
HCID70650982

未命名化合物

收率 44.6%

AUXILIARIES

试剂、催化剂与溶剂

1
反应SMILES：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of 7-acetyl-4-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (45 mg, 0.092 mmol) in tetrahydrofuran (10 mL) at 0° C. was added methylmagnesium bromide (0.154 mL, 0.462 mmol). The mixture was stirred at room temperature for 30 min. Additional methylmagnesium bromide (0.100 mL, 0.300 mmol) was added at 0° C., and the mixture was stirred at room temperature for another 30 min. The reaction was quenched with water (10 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (25 mL) and dried over anhydrous MgSO4. The organic solution was concentrated under vacuum, and the residue was purified by reverse phase HPLC. The correct fraction was concentrated under vacuum, basified with saturated NaHCO3 solution, and extracted with ethyl acetate (3×35 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (20.9 mg, 0.041 mmol, 44.1% yield) as a pale yellow solid. LCMS (M+H)+=504.0. 1H NMR (500 MHz, DMSO-d6) (recognizable peaks for the major atropisomer) δ: 11.74 (s, 1H), 8.44 (s, 1H), 8.23 (s, 1H), 8.30 (s, 1H), 7.98 (m, 1H), 7.92 (m, 1H), 7.80 (m, 1H), 7.75 (m, 1H), 7.58 (m, 1H), 7.24 (m, 1H), 5.12 (s, 1H), 1.83 (s, 3H), 1.50 (s, 6H).

WORKUP

后处理

  1. stirringthe mixture was stirred at room temperature for another 30 min
  2. customThe reaction was quenched with water (10 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  4. extractionThe combined extract
  5. washwas washed with brine (25 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationThe organic solution was concentrated under vacuum
  8. customthe residue was purified by reverse phase HPLC
  9. concentrationThe correct fraction was concentrated under vacuum
  10. extractionextracted with ethyl acetate (3×35 mL)
  11. extractionThe combined extract
  12. washwas washed with brine (30 mL)
  13. dry with materialdried over anhydrous MgSO4
  14. customRemoval of solvent under vacuum