(Diethylamino)sulfur trifluoride → HCID 58574838, compound

HRID 1619358Notes

Reaction equation

HRID 1619358 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[N:7]3[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:25])CC>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[N:7]3[CH2:16][CH2:15][CH:14]([F:25])[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58574537HCID 58574537, compound

Product 1

HCID 58574838HCID 58574838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 3-bromo-8-hydroxy-7,8,9,10-tetrahydroazepino[2,1-b]-quinazolin-12(6H)-one (200 mg, 0.64 mmol, 1 equiv) in DCM was added excess DAST under N2 at −78° C. After that, the resulting mixture was stirred at −78° C. for 3 h. The reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extract was dried over Na2SO4. After filtration and concentration, the crude product was purified by silica gel chromatography to give 200 mg of the desired product. MS (ESI): 311, 313 (MH+).

Workup

  1. customThe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dbe4e18ea1624365aa951a9bab34cec2
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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