Thiophenol → HCID 59379930, compound

HRID 2353646Notes

Reaction equation

HRID 2353646 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[CH:31]=[C:30]([CH2:32]OS(C)(=O)=O)[N:29]=[C:28]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][C:45]([NH:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:46])=[CH:40][CH:39]=2)[N:27]=1>C(#N)C>[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[CH:31]=[C:30]([CH2:32][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:29]=[C:28]([C:38]2[CH:39]=[CH:40][C:41]([NH:44][C:45]([NH:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:46])=[CH:42][CH:43]=2)[N:27]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59380001HCID 59380001, compound

Product 1

HCID 59379930HCID 59379930, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thiophenol (0.029 mL) was dissolved in Acetonitrile (3 mL). DBU (0.043 mL) was then added to the solution and was allowed to stir at RT for 15 minutes. 1-[4-[4-[(3S)-3-Methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidin-2-yl]phenyl]-3-phenyl-urea (80 mg) was added to the reaction and stirred for 30 minutes. The reaction was concentrated in vacuo and the residue chromatographed on silica, eluting with 5% methanol in DCM, to give the desired material (62 mg) as a white solid, Mass Spectrum; M+H+ 512.

Workup

  1. stirringstirred for 30 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with 5% methanol in DCM

Sources & evidence

ORD record
ord-0fac4b7a679948619f0df62162463df1
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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