Morpholine → HCID 53379768, compound

HRID 1771569Notes

Reaction equation

HRID 1771569 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:31]([CH3:34])(=[O:33])=[O:32])=[C:6]([C:8]2[N:13]=[C:12](S(C)(=O)=O)[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH2:28][CH2:29][OH:30])=[O:26])=[CH:20][CH:19]=3)[CH:9]=2)[CH:7]=1.CCN(C(C)C)C(C)C.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:31]([CH3:34])(=[O:32])=[O:33])=[C:6]([C:8]2[N:13]=[C:12]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[N:11]=[C:10]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25]([NH:27][CH2:28][CH2:29][OH:30])=[O:26])=[CH:22][CH:23]=3)[CH:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 67382529HCID 67382529, compound

Product 1

HCID 53379768HCID 53379768, compoundYield 5%

Procedure

1-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(methylsulfonyl)pyrimidin-4-yl)phenyl)-3-(2-hydroxyethyl)urea (275 mg, 0.23 mmol), DIPEA (804, 0.46 mmol) and morpholine (1.0 mL) were heated in a Biotage microwave at 100° C. for 30 minutes. Reaction mixture was partitioned between DCM and water, the organic phase passed through a PTFE hydrophobic frit and the solvent removed in vacuo. The residue was purified further by prep HPLC (low pH) to afford 1-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-morpholinopyrimidin-4-yl)phenyl)-3-(2-hydroxyethyl)urea (5.6 mg, 5%).

Workup

  1. customReaction mixture
  2. customwas partitioned between DCM and water
  3. customthe solvent removed in vacuo
  4. customThe residue was purified further by prep HPLC (low pH)

Sources & evidence

ORD record
ord-18a37bfef56c4b8aaeae8f1fdb9eebf3
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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