Triethylamine → HCID 25159520, compound

HRID 2198275Notes

Reaction equation

HRID 2198275 reaction equation
[CH2:1]1[CH:8]2[C:4]3([C:10]([NH:12][C:13]4[C:14]([C:19](O)=[O:20])=[N:15][CH:16]=[CH:17][CH:18]=4)=[O:11])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.[F:52][C:53]1([F:57])[CH2:56][NH:55][CH2:54]1>CN(C)C=O.C(OCC)(=O)C>[F:52][C:53]1([F:57])[CH2:56][N:55]([C:19]([C:14]2[C:13]([NH:12][C:10]([C:4]34[CH2:5][CH:6]5[CH2:9][CH:2]([CH2:1][CH:8]3[CH2:7]5)[CH2:3]4)=[O:11])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:20])[CH2:54]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68795224HCID 68795224, compound

Product 1

HCID 25159520HCID 25159520, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 332B (0.1 g, 0.35 mmol) in dimethylformamide (5 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.1 g, 0.52 mmol), 1-hydroxybenzotriazole hydrate (0.07 g, 0.52 mmol), triethylamine (0.11 g, 1.05 mmol) and 3,3-difluoro-azetidine hydrochloride (0.07 g, 0.52 mmol). The reaction was stirred at room temperature for 16 hours, diluted with ethyl acetate (50 mL) and the organics were washed with sodium bicarbonate solution, brine, dried over MgSO4, filtered, and concentrated. Flash chromatography (20% ethyl acetate in hexane) afforded the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ ppm 1.50-1.73 (m, 4H) 1.73-1.93 (m, 4H) 1.95-2.19 (m, 2H) 2.33 (s, 2H) 2.67 (t, J=6.61 Hz, 1H) 4.53 (t, J=12.37 Hz, 2H) 5.03 (t, J=12.54 Hz, 2H) 7.57 (dd, J=8.65, 4.58 Hz, 1H) 8.30 (dd, J=4.41, 1.36 Hz, 1H) 8.98 (dd, J=8.65, 1.53 Hz, 1H) 11.82 (s, 1H). MS (ESI+) m/z 362.1 (M+H)+

Workup

  1. washthe organics were washed with sodium bicarbonate solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab58ae197b6c4ef18ef49e18f73ecc71
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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