(Diethylamino)sulfur trifluoride → HCID 23518324, compound

HRID 1245515Notes

Reaction equation

HRID 1245515 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:32])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:23][C@H:22]([CH2:24][O:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][O:27]4)[C@@H:14]([O:15][CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][O:17]4)[C@@H:12]3O)[C:6]=2[N:7]=1.C(N(S(F)(F)[F:39])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([Cl:32])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:23][C@H:22]([CH2:24][O:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][O:27]4)[C@@H:14]([O:15][CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][O:17]4)[C@H:12]3[F:39])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 23518327HCID 23518327, compound

Product 1

HCID 23518324HCID 23518324, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the compound from Step G (0.24 g, 0.51 mmol) in CH2Cl2 (5 mL) and pyridine (0.8 mL) at −60° C. was added diethylaminosulfur trifluoride (DAST; 0.27 mL) dropwise under Ar. The solution was stirred at −60° C. for 0.5 h, at 0° C. overnight and at room temperature for 3h. The mixture was diluted with CH2Cl2 (25 mL) and poured into saturated aqueous NaHCO3 (15 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and evaporated. The residue was purified on a silica gel column with a solvent system of hexanes/EtOAc: 5/1 to give the title compound (45 mg) as a pale yellow foam.

Workup

  1. washThe organic layer was washed with water (10 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified on a silica gel column with a solvent system of hexanes/EtOAc

Sources & evidence

ORD record
ord-ecddbaa05d1547e688a43c750b59c371
Source dataset
uspto-grants-2006_10
Patent number
US07125855B2

Reaction notes

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