(Diethylamino)sulfur trifluoride → HCID 58574311, compound

HRID 1619316Notes

Reaction equation

HRID 1619316 reaction equation
O[CH:2]1[CH2:15][N:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]2=[O:16])=[CH:11][CH:10]=[C:9]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:8]=3)[CH2:4][CH2:3]1.CCN(S(F)(F)[F:31])CC>C(Cl)Cl>[F:31][CH:2]1[CH2:15][N:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]2=[O:16])=[CH:11][CH:10]=[C:9]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:8]=3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 58574163HCID 58574163, compound

Product 1

HCID 58574311HCID 58574311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-hydroxy-3-(pyridin-2-ylethynyl)-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (100 mg, 0.315 mmol, 1 eq) in DCM was added excess DAST under N2 at −78° C. After stirring at the same temperature for 3 hours, the reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the desired product, which was purified by silica gel chromatography. MS (ESI): 320 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 8.65-8.65 (d, J=3.30 Hz, 1H), 8.17-8.14 (d, J=8.16 Hz, 1H), 7.92-7.87 (t, J=7.5 Hz, 1H), 7.79 (s, 1H), 7.74-7.72 (d, J=7.71 Hz, 1H), 7.67-7.64 (d, J=8.04 Hz, 1H), 7.48-7.47 (m, 1H), 5.50-5.34 (d, J=48.6 Hz, 1H), 4.62-4.52 (t, J=15.9 Hz, 1H), 3.93-3.79 (dd, J=38.1, 15.3 Hz, 1H), 2.96-2.94 (m, 2H), 2.45-2.10 (m, 2H).

Workup

  1. customthe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8b9f6f390d14c22918effa330d72adb
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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