Sulfamide → HCID 53473393, compound

HRID 2037453Notes

Reaction equation

HRID 2037453 reaction equation
[NH2:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[S:34](N)([NH2:37])(=[O:36])=[O:35]>O1CCOCC1>[NH2:37][S:34]([NH:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:17][CH:18]=2)[CH3:12])[CH2:6][CH2:5]1)(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 53473235HCID 53473235, compound

Product 1

HCID 53473393HCID 53473393, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-6-(2-aminoethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluoro phenyl)-1,3-oxazinan-2-one (40 mg, 0.09 mmol) and sulfamide (44 mg, 0.45 mmol) in 1,4-dioxane (10 mL) was heated to reflux overnight. When the reaction was over, the solvent was removed to give the residue, which was purified by preparative HPLC to give the desired product (12 mg, 25%). 1H NMR (CDCl3): 1.54 (m, 3H), 2.26 (m, 5H), 3.08 (m, 3H), 4.56 (s, 2H), 5.67 (m, 1H), 6.89 (m, 2H), 7.05 (m, 4H), 7.28 (m, 5H). LC-MS Method 3 tR=1.24 min, m/z=534.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customwas removed
  4. customto give the residue, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-5ba4369fe64540b8a3d7b87043761ba1
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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