Acetylcysteamine → HCID 59379888, compound

HRID 2353645Notes

Reaction equation

HRID 2353645 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][SH:7])(=[O:3])[CH3:2].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[N:27]=[C:28]([C:38]2[CH:39]=[CH:40][C:41]([NH:44][C:45](=[O:46])[NH:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[CH:42][CH:43]=2)[N:29]=[C:30]([CH2:32][S:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:31]=1

Participants

5

Reactant 3

HCID 14484AcetylcysteamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59380001HCID 59380001, compound

Product 1

HCID 59379888HCID 59379888, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N-Acetylcysteamine (0.086 mL) was dissolved in acetonitrile (5 mL). DBU (0.120 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 (228 mg) in acetonitrile (5 mL) was added to the reaction and stirred for 30 minutes. The reaction was concentrated in vacuo and the crude residue purified on silica, eluting with 5% methanol in DCM, to give the desired compound (100 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-e172335068bf4e948c9bed6361074134
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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