(Diethylamino)sulfur trifluoride → HCID 89570397, compound

HRID 530114Notes

Reaction equation

HRID 530114 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[C:7](=[O:20])[C@@H:6]([CH2:21]O)[N:5]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:4]=2[N:3]=1.C(N(S(F)(F)[F:34])CC)C>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[C:7](=[O:20])[C@@H:6]([CH2:21][F:34])[N:5]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 89570395HCID 89570395, compound

Product 1

HCID 89570397HCID 89570397, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[(7R)-2-chloro-8-cyclopentyl-7-(hydroxymethyl)-6-oxo-7,8-dihydropteridin-5(6H)-yl]benzonitrile (94 mg, 0.24 mmol) in anhydrous DCM (3 mL) was added diethylaminosulfur trifluoride (39 μL, 0.29 mmol) at −78° C. under nitrogen. The mixture was allowed to warm to rt and stirred for 18 h. The mixture was then cooled to 0° C. and quenched by saturated aqueous NaHCO3 solution. The mixture was extracted with DCM (30 mL×2) and the combined organic layers were dried over Na2SO4, concentrated in vacuo to give a crude residue, which was purified using a silica gel flash chromatography [eluent: 0-50% EtOAc/Heptane] to afford the desired compound (24 mg, 25%). 1H NMR (400 MHz, CD3OD): δ 7.89-7.94 (m, 1H), 7.74-7.80 (m, 2H), 7.61-7.66 (m, 1H), 7.01 (s, 1H), 4.87-5.00 (m, 1H), 4.70-4.83 (m, 1H), 4.31 (quin, J=8.4 Hz, 1H), 2.08-2.19 (m, 2H), 1.97-2.07 (m, 4H), 1.61-1.76 (m, 2H). MS (ES+): m/z=386.32/388.29 [MH+]. UPLC: tR=1.33 min (TOF: polar_2 min).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customquenched by saturated aqueous NaHCO3 solution
  3. extractionThe mixture was extracted with DCM (30 mL×2)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue, which
  7. customwas purified

Sources & evidence

ORD record
ord-de31b63bdf144346ab4ba375fafef51a
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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