Dimethyl Sulfoxide → HCID 68697190, compound

HRID 1161648Notes

Reaction equation

HRID 1161648 reaction equation
Cl.Cl.[CH:3]12[CH2:14][CH:10]([CH2:11][NH:12][CH2:13]1)[C:9]1[CH:8]=[CH:7][C:6]([NH:15][C:16]3[N:21]=[C:20]([NH:22][CH:23]4[CH2:25][CH2:24]4)[C:19]([C:26]([F:29])([F:28])[F:27])=[CH:18][N:17]=3)=[CH:5][C:4]2=1.CC[N:32]([CH:36]([CH3:38])C)[CH:33]([CH3:35])C.O.[CH3:40]S(C)=O>>[CH:23]1([NH:22][C:20]2[C:19]([C:26]([F:28])([F:29])[F:27])=[CH:18][N:17]=[C:16]([NH:15][C:6]3[CH:7]=[CH:8][C:9]4[CH:10]5[CH2:14][CH:3]([CH2:13][N:12]([C:36]6[CH:38]=[CH:40][CH:35]=[CH:33][N:32]=6)[CH2:11]5)[C:4]=4[CH:5]=3)[N:21]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 81531DiisopropylethylamineHCID 68692475HCID 68692475, compound

Product 1

HCID 68697190HCID 68697190, compoundYield 49%

Conditions

Temperature
130 °C

Procedure

Compound 13 (290 mg, 645 μmol) was dissolved in DMSO (2 mL) in a 15 mL screw cap pressure tube, and the resultant solution was treated with DIEA (431 μL, 2.48 mmol) and 2-fluoropyride (125 mg, 1.29 mmol). The reaction vessel was sealed and stirred at 130° C. for 14 hours. The reactor contents were cooled to 25° C., poured into H2O (30 mL), and stirred for 1 hour to produce an orange, gummy residue. The H2O was decanted off and the residue purified on silica gel (40% EtOAc/Hexanes) to provide 14 as an off-white powder (143 mg, 49% yield). HPLC Rt 6.57 minutes; LC/MS (Method F) m/z 453.3 (MH+).

Workup

  1. customscrew cap pressure tube
  2. customThe reaction vessel was sealed
  3. temperatureThe reactor contents were cooled to 25° C.
  4. stirringstirred for 1 hour
  5. customto produce an orange, gummy residue
  6. customThe H2O was decanted off
  7. customthe residue purified on silica gel (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-3ae38ec8f17d47faa0e93f26564e7fca
Source dataset
uspto-grants-2010_10
Patent number
US07820648B2

Reaction notes

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