Water → N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-4-(4H-1,2,4-triazol-4-yl)aniline

HRID 1039071Notes

Reaction equation

HRID 1039071 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][N:19]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH:33]=[N:32][N:31]=[CH:30]4)=[CH:25][CH:24]=3)C(=O)C)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][NH:19][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH:30]=[N:31][N:32]=[CH:33]4)=[CH:27][CH:28]=3)[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67777386N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide

Product 1

HCID 50939921N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-4-(4H-1,2,4-triazol-4-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide from step 1 of this example was dissolved in ethanol (0.5 mL), added sodium hydroxide (60% w/w, 0.3 mL) and heated to 80° C. for 5.5 hours. The reaction was cooled to room temperature, water (10 mL) was added and extracted with ethyl acetate (20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 50% acetone/hexanes to give the title compound as a white-solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (20 mL)
  3. dry with materialThe organic phase was dried by magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge
  7. washeluting with 50% acetone/hexanes

Sources & evidence

ORD record
ord-5da9ebe80682400ebd0c0b0b5b20b2ab
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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