Sodium Hydroxide → HCID 58557408, compound

HRID 1969627Notes

Reaction equation

HRID 1969627 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:5][CH:4]1[C:18]1[N:22]2[C:23]3[CH:29]=[CH:28][NH:27][C:24]=3[N:25]=[CH:26][C:21]2=[N:20][N:19]=1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[Na+].[H-].[Na+].[CH3:67][Si:68]([CH2:71][CH2:72][O:73][CH2:74]Cl)([CH3:70])[CH3:69]>O1CCOCC1>[CH2:1]([CH:3]1[CH2:7][CH:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:5][CH:4]1[C:18]1[N:22]2[C:23]3[CH:29]=[CH:28][N:27]([CH2:74][O:73][CH2:72][CH2:71][Si:68]([CH3:70])([CH3:69])[CH3:67])[C:24]=3[N:25]=[CH:26][C:21]2=[N:20][N:19]=1)[CH3:2]

Participants

8

Reactant 6

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136009314HCID 136009314, compound

Product 1

HCID 58557408HCID 58557408, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-(2-ethyl-4-(4-methoxybenzyloxy)cyclopentyl)-6H-pyrrolo[2,3-e][1,2,4]-triazolo[4,3-a]pyrazine (0.323 g, 0.825 mmol, prepared using Z from Preparation #EE.1, A from Example #1, Step D, HATU, and TEA, B with DIEA, D with NaOH) in 1,4-dioxane (2.5 mL) was added NaH (0.035 g, 0.866 mmol, 60% dispersion in mineral oil) in portions. The reaction mixture was stirred at ambient temperature for about 30 min. SEM-Cl (0.15 mL, 0.83 mmol) was added. After about 30 min, the solvent was removed and the residue was partitioned between EtOAc (12 mL) and water (2 mL). The organic layer was separated and concd under reduced pressure. The residue was purified using silica gel chromatography (40 g) eluting with a gradient of 0-60% EtOAc in DCM to give 1-(2-ethyl-4-(4-methoxybenzyloxy)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.372 g, 86%): LC/MS (Table 1, Method b) Rt=2.96 min; MS m/z: 522 (M+H)+.

Workup

  1. customprepared
  2. customfrom Preparation #EE.1
  3. waitAfter about 30 min
  4. customthe solvent was removed
  5. customthe residue was partitioned between EtOAc (12 mL) and water (2 mL)
  6. customThe organic layer was separated
  7. customThe residue was purified
  8. washeluting with a gradient of 0-60% EtOAc in DCM

Sources & evidence

ORD record
ord-56120f09432e42c28d43b99d9e8cae67
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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