Ammonium Hydroxide → HCID 66583264, compound

HRID 1972640Notes

Reaction equation

HRID 1972640 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:34]>CCO>[NH2:34][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C@@:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86670420HCID 86670420, compound

Product 1

HCID 66583264HCID 66583264, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a 20-mL vial was added (2S)-2-(4-(4-((6-chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.235 g, 0.482 mmol), EtOH (3.0 mL), and ammonium hydroxide (30%, 3.0 mL, 23 mmol, J. T. Baker, Philipsburg, N.J.). The vial was sealed and heated at 110° C. for 20 h. The reaction mixture was cooled to rt and the solvent was removed in vacuo. The residue was partitioned between water (20 mL) and DCM (40 mL). The aqueous layer was extracted with DCM (2×20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (40 g of silica, 10 to 30% acetone in hexanes) to afford (2S)-2-(4-(4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (0.180 g) as a mixture of two isomers.

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was cooled to rt
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between water (20 mL) and DCM (40 mL)
  5. extractionThe aqueous layer was extracted with DCM (2×20 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (40 g of silica, 10 to 30% acetone in hexanes)

Sources & evidence

ORD record
ord-66e263e077cd4f5cab0132e215a658f7
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…