Sodium Carbonate → HCID 136147411, compound

HRID 467500Notes

Reaction equation

HRID 467500 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]3[C:27]([C:28]4[O:32][N:31]=[C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:29]=4)=[CH:26][N:25](S(C4C=CC(C)=CC=4)(=O)=O)[C:22]3=[N:23][CH:24]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])([CH3:9])[CH3:8]>C1COCC1>[CH:7]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]3[C:27]([C:28]4[O:32][N:31]=[C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:29]=4)=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)=[CH:17][CH:18]=1)(=[O:11])=[O:12])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 66762780HCID 66762780, compound

Product 1

HCID 136147411HCID 136147411, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2M Na2CO3 (136 μL, 0.272 mmol) was added to a stirred solution of 5-[2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazin-7-yl]-3-phenyl-isoxazole (40.7 mg, 0.06798 mmol) in THF (4.6 mL) and the reaction stirred at ambient temperature for 64 hours. The reaction mixture was partitioned between EtOAc/brine and the layers separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic extracts dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from MeCN and the precipitate isolated by filtration to give the title compound as a yellow solid (20.3 mg, 67% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.16 (s, 6H), 3.52 (t, 1H), 7.52-7.61 (m, 4H), 8.02-8.05 (m, 4H), 8.63 (d, 2H), 8.69 (s, 1H), 9.18 (s, 1H) and 13.00 (br s, 1H) ppm; MS (ES+) 445.1.

Workup

  1. customThe reaction mixture was partitioned between EtOAc/brine
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with EtOAc (×2)
  4. dry with materialthe combined organic extracts dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated from MeCN
  8. customthe precipitate isolated by filtration

Sources & evidence

ORD record
ord-a260ab2c502f4bc79697d6d1ecd379c6
Source dataset
uspto-grants-2014_01
Patent number
US08623869B2

Reaction notes

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