Ammonium Hydroxide → HCID 68908622, compound

HRID 2198253Notes

Reaction equation

HRID 2198253 reaction equation
[CH3:1][C:2]1[C:3]([C:18]([OH:20])=O)=[C:4]([NH:8][C:9]([CH:11]2[C:13]([CH3:15])([CH3:14])[C:12]2([CH3:17])[CH3:16])=[O:10])[S:5][C:6]=1[CH3:7].C([N:24](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[OH-]>O1CCCC1>[CH3:1][C:2]1[C:3]([C:18]([NH2:24])=[O:20])=[C:4]([NH:8][C:9]([CH:11]2[C:13]([CH3:15])([CH3:14])[C:12]2([CH3:17])[CH3:16])=[O:10])[S:5][C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66475500HCID 66475500, compound

Product 1

HCID 68908622HCID 68908622, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 9B (0.30 g, 1.0 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) in 5 mL tetrahydrofuran was added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.41 g, 1.1 mmol). The mixture stirred for 2 hours at ambient temperature, and 5 mL of NH4OH was added and the reaction mixture stirred for an additional 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in 10 mL CH2Cl2. NH4Cl (5 mL) was added, the layers were separated and the aqueous layer was extracted 2×5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered, concentrated, and purified via column chromatography (SiO2, 50% hexanes:ethyl acetate) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.15 (s, 1H), 1.21 (s, 6H), 1.32 (s, 6H), 2.26 (s, 3H), 2.30 (s, 3H), 5.60-5.84 (m, 2H), 11.88 (s, 1H); MS (DCI/NH3) m/z 295 (M+H)+; anal. calculated for C15H22N2O2S: C, 61.19; H, 7.53; N, 9.52. Found: C, 61.28; H, 7.74; N, 9.44.

Workup

  1. stirringthe reaction mixture stirred for an additional 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 10 mL CH2Cl2
  4. additionNH4Cl (5 mL) was added
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted 2×5 mL CH2Cl2
  7. dry with materialThe combined organics were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified via column chromatography (SiO2, 50% hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-ebfac3c416004b1ebe8c774bc92262f5
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

Loading…