Ammonia → HCID 11648720, compound

HRID 853849Notes

Reaction equation

HRID 853849 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@H:18]3[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:16])=[O:15])=[CH:11][CH:12]=2)[C:7]2([O:34][CH2:33][CH2:32][CH2:31][O:30]2)[C:6]1=O.N>CCO>[O:23]([CH2:22][C@@H:18]1[CH2:19][CH2:20][CH2:21][N:17]1[S:14]([C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[CH2:4][CH2:3][CH2:2][N:1]=[C:6]3[C:7]3([O:34][CH2:33][CH2:32][CH2:31][O:30]3)[C:8]=2[CH:9]=1)(=[O:16])=[O:15])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58932560HCID 58932560, compound

Product 1

HCID 11648720HCID 11648720, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
135 °C

Procedure

1′-(3 -Aminopropyl)-5′-{[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (0.98 g, 1.95 mmol) was taken up in 2M EtOH.NH3 (100 mL) poured into a steel pressure bottle and heated at 135° C. for 20.5 hr. The mixture was cooled to room temperature and concentrated. The residue was washed with H2O (3×), brine (2×), dried over MgSO4, and filtered. The filtrate was flash chromatographed (Biotage KP silica gel, CH2Cl2/CH3OH/NH4OH (98.5/1.0/0.5)) to give the title compound as a white solid (0.73 g, 77% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (APCI+) m/z 483 [M+H]. Opt. Rotation: −169.0 (calculated) at 25° C. in CHCl3 (1% concentration) at 589 nM.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. washThe residue was washed with H2O (3×), brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customchromatographed (Biotage KP silica gel, CH2Cl2/CH3OH/NH4OH (98.5/1.0/0.5))

Sources & evidence

ORD record
ord-bfc7548876bd41a59ca96104b74d4b43
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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