Cesium carbonate → HCID 59374056, compound

HRID 473735Notes

Reaction equation

HRID 473735 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[C:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[N:26][CH:25]=[CH:24][N:23]=1>>[CH:28]1([C:27]2[C:22]([O:14][C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:9][CH:10]=3)=[N:23][CH:24]=[CH:25][N:26]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 20528946HCID 20528946, compoundHCID 212625714-(Pyridin-2-ylamino)phenol

Product 1

HCID 59374056HCID 59374056, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(pyridin-2-ylamino)phenol (0.30 g, 1.60 mmol), cesium carbonate (1.56 g, 4.80 mmol), and 2-chloro-3-cyclopentylpyrazine (0.29 g, 1.60 mmol) under argon was heated to 120° C. for 20 h. The mixture was cooled to RT and partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with aqueous 1N sodium hydroxide (2×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give N-(4-(3-cyclopentylpyrazin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 333.3 (M+1). IC50 (uM) 0.012.

Workup

  1. temperatureThe mixture was cooled to RT
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with aqueous 1N sodium hydroxide (2×), saturated aqueous sodium chloride (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d01dc1e3fe9473b8daf6cf9cd82e01b
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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