Water → HCID 50939526, compound

HRID 1039056Notes

Reaction equation

HRID 1039056 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][NH2:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][N:28]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][NH:19][C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][N:28]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 98994832-Bromo-5-(methylsulfonyl)pyridineHCID 677784742-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

Product 1

HCID 50939526HCID 50939526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine (35 mg, 0.125 mmol) from Example 5 step 3 was dissolved in DMF (0.62 mL), cesium carbonate (203 mg, 0.62 mmol) was added, stirred at room temperature for 10 minutes. 2-bromo-5-(methylsulfonyl)pyridine (32.4 mg, 0.137 mmol) was added. Reaction was run at room temperature for 1 hour, then heated to 50° C. for 5 hours. Water (10 mL) was added, extracted with EtOAc (10 mL×2), second wash with brine (10 mL). The organic phase was dried by magnesium sulfate, filter, concentrated and purified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm) using 30% acetone/hexane to give the title compound as a white solid.

Workup

  1. customReaction
  2. waitwas run at room temperature for 1 hour
  3. temperatureheated to 50° C. for 5 hours
  4. extractionextracted with EtOAc (10 mL×2)
  5. washsecond wash with brine (10 mL)
  6. dry with materialThe organic phase was dried by magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrated
  9. custompurified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm)

Sources & evidence

ORD record
ord-baa23bd31e0244ab998cba882b62cb06
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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