(Diethylamino)sulfur trifluoride → HCID 86689497, compound

HRID 1853801Notes

Reaction equation

HRID 1853801 reaction equation
O[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]3[C:16]4[CH:29]=[CH:28][S:27][C:17]=4[C:18](=[O:26])[NH:19][C:20]=3[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])=[CH:10][CH:9]=1)(=[O:7])=[O:6].CCN(S(F)(F)[F:36])CC>C(Cl)Cl.C1COCC1>[F:36][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]3[C:16]4[CH:29]=[CH:28][S:27][C:17]=4[C:18](=[O:26])[NH:19][C:20]=3[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67450881HCID 67450881, compound

Product 1

HCID 86689497HCID 86689497, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (120 mg, 0.28 mmol) in methylene chloride (10 mL) and THF (6 mL) under nitrogen at −78° C. was added DAST (89 mg, 0.56 mmol) and the reaction mixture was stirred at −78° C. for 2 h and warmed to room temperature and stirred for 16 h. The reaction mixture was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/hexanes gradient). The resulting crude residue was triturated in methylene chloride and filtered to afford the desired product (90 mg, 75%) as a off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.92 (s, 1H), 8.10 (t, J=5.9 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.43 (d, J=9.2 Hz, 1H), 5.75 (d, J=5.4 Hz, 1H), 4.51 (t, J=4.9 Hz, 1H), 4.42 (t, J=4.9 Hz, 1H), 3.71 (s, 3H), 3.24 (q, J=5.2 Hz, 1H), 3.19 (q, J=5.2 Hz, 1H); ESI MS m/z 433 [C20H17FN2O4S2+H]+; HPLC 93.4% (AUC), tR=15.64 min.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by column chromatography (silica gel, ethyl acetate/hexanes gradient)
  5. customThe resulting crude residue was triturated in methylene chloride
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ac1523b235154465a7779c49c59c8549
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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