Water → HCID 50939660, compound

HRID 1039059Notes

Reaction equation

HRID 1039059 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]([N:38]2[CH:42]=[CH:41][N:40]=[N:39]2)=[CH:34][N: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]([N:38]4[CH:42]=[CH:41][N:40]=[N:39]4)=[CH:34][N:33]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 581285562-fluoro-5-(1H-1,2,3-triazol-1-yl)pyridineHCID 677784742-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

Product 1

HCID 50939660HCID 50939660, 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 2 step 3 was dissolved in NMP (0.21 mL), DBU (24.4 mg, 0.16 mmol) was added, stirred at room temperature for 10 minutes. 2-fluoro-5-(1H-1,2,3-triazol-1-yl)pyridine (21 mg, 0.13 mmol; from step 2 of this example) was added. Reaction was heated to 110° C. for 3 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 column chromatography through a 12 gram RediSep Rf™ silica gel cartridge eluting with 30% ethylacetate/hexanes to give the title compound as a white solid.

Workup

  1. customReaction
  2. temperaturewas heated to 110° C. for 3 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 by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge
  10. washeluting with 30% ethylacetate/hexanes

Sources & evidence

ORD record
ord-e9d17d8f939d4af9be55b205fb2c5a0a
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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