Cesium carbonate → HCID 67419373, compound

HRID 2035399Notes

Reaction equation

HRID 2035399 reaction equation
[Si](O[CH2:19][C:20]1[CH:21]=[C:22]([C@H:27]2[C@@H:32]([OH:33])[C@@H:31]([OH:34])[C@H:30]([OH:35])[CH:29]([CH2:36][OH:37])[O:28]2)[CH:23]=[CH:24][C:25]=1Cl)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]2[N:43]([C:45](=[O:48])[NH:46][N:47]=2)[CH:44]=1.[C:49](=O)([O-])[O-:50].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CO.ClCCl.CO>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]2[N:43]([C:45](=[O:48])[N:46]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:50][CH3:49])=[C:22]([C@H:27]4[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@H:30]([OH:35])[C@@H:29]([CH2:36][OH:37])[O:28]4)[CH:21]=3)[N:47]=2)[CH:44]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 12040793HCID 12040793, compoundHCID 67417642HCID 67417642, compound

Product 1

HCID 67419373HCID 67419373, compoundYield 39.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product (83 mg, 0.15 mmol) from step B and 6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (29.3 mg, 0.17 mmol) in DMF (5.0 mL) was added cesium carbonate (0.11 g, 0.35 mmol) and then heated at 60° C. overnight. The reaction solution was cooled to room temperature, diluted with methanol (10 mL) and added potassium carbonate (43.2 mg, 0.31 mmol) to it. The resultant mixture was stirred at room temperature until complete loss of starting material. The reaction solution was then diluted with 9:1 mixture of dichloromethane/methanol, filtered through a syringe filter and concentrated in vacuo. The residue obtained was purified by preparative thin layer chromatography (dichloromethane/methanol 9:1) to give 6-chloro-2-(4-methoxy-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (26.7 mg, 39%): 1H NMR (CD3OD, 500 MHz) δ 7.94 (t, J=1.5 Hz, 1H), 7.48 (d, J=2.5 Hz, 1H), 7.30 (dd, J=8.5, 2.0 Hz, 1H), 7.20-7.17 (m, 2H), 6.95 (d, J=8.5 Hz, 1H), 5.09 (s, 2H), 4.68 (d, J=9.5 Hz, 1H), 3.84 (dd, J=12.0, 2.5 Hz, 1H), 3.80 (s, 3H), 3.65 (dd, J=12.0, 7.0 Hz, 1H), 3.53-3.45 (m, 2H), 3.42-3.35 (m, 2H); ESI MS m/z 452 [M+H]+.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered through a syringe
  3. filtrationfilter
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas purified by preparative thin layer chromatography (dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-6bdb94e0b4c146c3916e6ed84cd7e7e5
Source dataset
uspto-grants-2013_11
Patent number
US08575114B2

Reaction notes

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