Triethylamine → HCID 68543674, compound

HRID 2242176Notes

Reaction equation

HRID 2242176 reaction equation
[C:1]([CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2O)=[C:8]([C:18]([OH:20])=[O:19])[CH:7]=[N:6]1)([OH:3])=O.CCN=C=N[CH2:26][CH2:27][CH2:28][N:29]([CH3:31])C.[CH2:32]([N:34](CC)CC)C.CN(C(ON1N=N[C:49]2[CH:50]=[CH:51]C=N[C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:27]1([CH2:28][NH:29][CH2:31][CH2:32][NH:34][C:1](=[O:3])[CH2:4][N:5]2[C:9]3[C:10]4[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=4[O:20][C:18](=[O:19])[C:8]=3[CH:7]=[N:6]2)[CH2:26][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136338384HCID 136338384, compound

Product 1

HCID 68543674HCID 68543674, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound h was dissolved in DMF (2 mL) and to the solution was added EDCI and Triethylamine to the reaction mixture. The resultant solution was stirred for 6 h at rt. To the reaction mixture was then added HATU and triethyl amine and the reaction mixture was stirred further for another hour. After completion of the reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The organic solution was dried over Na2SO4 and concentrated to provide the product i. The crude product was purified by Preparative TLC using 10% TEA in ethyl acetate as mobile phase: LC MS (Method B): 397 (M+l); 1H NMR (400 MHz, CDCl3/TMS):δ 8.24 (s, 1H), 7.60 (s, 1H), 7.37 (s, 2H), 6.47 (bs, 1H), 5.28 (s, 2H), 3.21 (q, J=5.5 Hz, 2H), 2.46 (s, 3H), 2.33 (t, J=5.1 Hz, 2H), 2.06-1.98 (m, 1H), 2.00 (s, 3H), 1.69-1.66 (m, 2H), 1.58-1.49 (m, 2H), 1.10-0.89 (m, 6H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d2556332a23a464ea9e91bbf4ee02463
Source dataset
uspto-grants-2010_03
Patent number
US07671069B2

Reaction notes

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