Diisopropylethylamine → HCID 68233575, compound

HRID 1429370Notes

Reaction equation

HRID 1429370 reaction equation
[NH2:1][C@H:2]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:3][O:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9].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>CN(C=O)C>[C:17]([O:16][CH2:15][C@H:2]1[NH:1][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[CH2:5][O:4][CH2:3]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68233578HCID 68233578, compound

Product 1

HCID 68233575HCID 68233575, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 14d (394 mg, 1.4 mmol) and HATU (639 mg, 1.68 mmol) in DMF (20 mL) at rt was added DIPEA (1 mL). The reaction mixture is stirred for 16 h, quenched with H2O and extracted with EA (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by CC on silica gel, eluting with PE/EA=4:1 to give compound 14e (171 mg, 46% yield) as a yellow solid.

Workup

  1. customquenched with H2O
  2. extractionextracted with EA (100 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by CC on silica gel
  7. washeluting with PE/EA=4:1

Sources & evidence

ORD record
ord-c5779f7f1a4246b29439cad9235b82aa
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…