Water → HCID 67778566, compound

HRID 1039057Notes

Reaction equation

HRID 1039057 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.C1CCN2C(=NCCC2)CC1.F[C:32]1[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.O>CN1C(=O)CCC1>[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:32]3[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 677784742-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

Product 1

HCID 67778566HCID 67778566, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine (30 mg, 0.11 mmol) from Example 5 step 3 was dissolved in NMP (0.21 mL), DBU (24.4 mg, 0.16 mmol) was added, stirred at room temperature for 5 minutes. 1-fluoro-4-(methylsulfonyl)benzene (22.3 mg, 0.13 mmol) was added. Reaction was heated to 110° C. for 17 hours. The reaction was cooled down to room temperature, 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 purified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge eluting with 30% acetone/hexanes to give the title compound as a white solid.

Workup

  1. customReaction
  2. temperaturewas heated to 110° C. for 17 hours
  3. temperatureThe reaction was cooled down to room temperature
  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
  10. customby purified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge
  11. washeluting with 30% acetone/hexanes

Sources & evidence

ORD record
ord-19bb495f1c8a4b2cac9638aeb7b52e5c
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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