1,2,3,4-Tetrahydroquinoline → HCID 59467900, compound

HRID 1404950Notes

Reaction equation

HRID 1404950 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][CH2:38]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[N:37]1([C:3](=[O:5])[CH2:2][NH:1][C:6](=[O:7])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 694601,2,3,4-TetrahydroquinolineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59467900HCID 59467900, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Boc-Gly-OH (80) (4.0 g, 22.83 mmol) in dry CH2Cl2 (50 mL) at 0° C. under N2 was added HATU (8.70 g, 22.9 mmol). After stirring for 15 min at r.t., 1,2,3,4-tetrahydroquinoline (2.9 mL, 23.0 mmol), and DIPEA (12 mL, 68.8 mmol) were added. The reaction was stirred for 36 h at room temperature. The reaction mixture was diluted with CH2Cl2 (100 mL) and washed with saturated NaHCO3, 5% HCl, water, and saturated NaCl. Dried over MgSO4, and filtered. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-50% EtOAc in hexanes) to afford 81 as a solid (5.76 g, 87%).

Workup

  1. stirringThe reaction was stirred for 36 h at room temperature
  2. washwashed with saturated NaHCO3, 5% HCl, water, and saturated NaCl
  3. dry with materialDried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe product was purified by column chromatography (10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a92a0e14cf64494380020b179ea5d418
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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