2-Propanethiol → HCID 59379894, compound

HRID 2353643Notes

Reaction equation

HRID 2353643 reaction equation
[CH:1]([SH:4])([CH3:3])[CH3:2].[CH3:5][C@H:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:12]1[CH:17]=[C:16]([CH2:18]OS(C)(=O)=O)[N:15]=[C:14]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:32])=[CH:26][CH:25]=2)[N:13]=1>C(#N)C.N12CCCN=C1CCCCC2>[CH3:5][C@H:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:12]1[CH:17]=[C:16]([CH2:18][S:4][CH:1]([CH3:3])[CH3:2])[N:15]=[C:14]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:32])=[CH:28][CH:29]=2)[N:13]=1

Participants

5

Reactant 2

HCID 63642-PropanethiolHCID 59380001HCID 59380001, compound

Product 1

HCID 59379894HCID 59379894, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

Isopropyl mercaptan (0.075 mL) was dissolved in acetonitrile (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.12 mL). The reaction was allowed to stir at room temperature for 15 minutes then 1-[4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidin-2-yl]phenyl]-3-phenyl-urea (228 mg) in acetonitrile (5 mL) added. The reaction was stirred for 30 minutes then concentrated in vacuo. The residue was chromatographed on silica, eluting with 2.5% methanol in DCM, to give the desired compound (78 mg) as a gum.

Workup

  1. stirringThe reaction was stirred for 30 minutes
  2. concentrationthen concentrated in vacuo
  3. customThe residue was chromatographed on silica
  4. washeluting with 2.5% methanol in DCM

Sources & evidence

ORD record
ord-2fc505725ca84203b50461a7e1dd8951
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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