Sodium Carbonate → HCID 86628364, compound

HRID 2233195Notes

Reaction equation

HRID 2233195 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2([OH:27])[C:23]3[C:24]4[N:15]([C:16](=[O:26])[CH:17]=[N:18][C:19]=4[CH:20]=[CH:21][C:22]=3[F:25])[CH2:14]2)(=O)=O)=CC=1.[O:28]1[C:37]2[CH:36]=[C:35]([CH2:38][N:39]([CH:47]3[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]3)[C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[N:34]=[CH:33][C:32]=2[O:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:28]1[C:37]2[CH:36]=[C:35]([CH2:38][N:39]([CH:47]3[CH2:52][CH2:51][N:50]([CH2:12][C:13]4([OH:27])[C:23]5[C:24]6[N:15]([C:16](=[O:26])[CH:17]=[N:18][C:19]=6[CH:20]=[CH:21][C:22]=5[F:25])[CH2:14]4)[CH2:49][CH2:48]3)[C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[N:34]=[CH:33][C:32]=2[O:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 578154611,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamateHCID 86628365HCID 86628365, compound

Product 1

HCID 86628364HCID 86628364, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (7-fluoro-6-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]quinoxalin-6-yl)methyl 4-methylbenzenesulfonate (0.093 g, 0.24 mmol) in ethanol (3 mL) was added 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)4-piperidinylcarbamate (for a synthesis see WO 2004058144 Example 99(h)) (78.5 mg, 0.22 mmol), then sodium carbonate (71.5 mg, 0.68 mmol). The reaction mixture was stirred at room temperature for 16 hours and evaporated to dryness. The residue was placed directly onto the top of a 20 g silica gel column and chromatographed eluting with a 0-100% ethyl acetate in petrol gradient, then with a 0-50% methanol in ethyl acetate gradient to afford the product (70 mg, 52%).

Workup

  1. customevaporated to dryness
  2. customchromatographed
  3. washeluting with a 0-100% ethyl acetate in petrol gradient

Sources & evidence

ORD record
ord-81f7205e1c064573a9785c39836738c2
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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