Carbon Dioxide → HCID 71264970, compound

HRID 2408760Notes

Reaction equation

HRID 2408760 reaction equation
[Li]CCCC.[C:6](=[O:8])=O.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CN(C(ON1N=N[C:25]2[CH:26]=[CH:27][CH:28]=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:39]1C[O:42][CH2:41][CH2:40]1>CN(C=O)C.O>[OH:42][CH2:41][C:40]1[CH:39]=[CH:28][C:27]([C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:26][C:25]=1[CH3:24]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 8082PiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178418339Butyllithium

Product 1

HCID 71264970HCID 71264970, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of R-5 (47 mmol, 9.5 g) in THF (2000 mL) at −78° C. is added n-BuLi (1.6M in hexanes, 104 mmol, 65 mL). The mixture is stirred for 15 min before the dry ice bath is removed. After 5 min dry ice is added. Water is added and the pH adjusted to 3 with 1N HCl. The mixture is saturated with NaCl and extracted with ethyl acetate (3×20 mL). Organics are combined and dried over MgSO4 and concentrated in vacuo. The crude is purified by flash chromatography to give R-6 (7.6 g, 97%). R-6 (7.2 mmol, 1.2 g) is dissolved in DMF (30 mL) followed by piperidine (36 mmol, 3.00 g) then HATU (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (8.7 mmol, 3.3 g). The mixture is stirred at ambient temperature for 3 h. Water is added and the mixture extracted with ethyl acetate. Organics are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC to yield the title intermediate (1.10 g, 65%).

Workup

  1. customis removed
  2. additionAfter 5 min dry ice is added
  3. additionWater is added
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude is purified by flash chromatography
  8. customto give R-6 (7.6 g, 97%)
  9. extractionthe mixture extracted with ethyl acetate
  10. washwashed with brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated in vacuo
  13. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-e96db9ceaa894c5e89a30c711bd77acc
Source dataset
uspto-grants-2014_08
Patent number
US08815857B2

Reaction notes

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