Diisopropylethylamine → HCID 58458903, compound

HRID 390339Notes

Reaction equation

HRID 390339 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([O:17][CH2:18][CH3:19])=[N:11][C:10]=1[C:20]([OH:22])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](=[NH:34])[NH:32]O)=[CH:26][CH:25]=1.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>O1CCOCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([O:17][CH2:18][CH3:19])=[N:11][C:10]=1[C:20]1[O:22][N:34]=[C:31]([CH2:30][C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[N:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58458909HCID 58458909, compoundHCID 178510821HCID 178510821, compound

Product 1

HCID 58458903HCID 58458903, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(benzyloxy)-2-ethoxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid (0.5045 g, 3 mmol), 2-(4-fluorophenyl)-N-hydroxyacetimidamide (0.9190, 3.02 mmol), HATU (1.255 g, 3.3 mmol) and DIEA (0.5 mL) in 1,4-dioxane (20 mL) was heated at 100° C. for 6 h. The mixture was cooled, diluted with EtOAc (50 mL), washed with water (10 mL), sat. NaHCO3 (10 mL), brine (10 mL), then dried (Na2SO4), filtered and concentrated to give a brown residue. This residue was purified by flash chromatography on a silica gel column using 7:3 Hexanes/EtOAc as eluant to afford the title compound product (0.68 g, 52% yield) as a yellow solid. 1HNMR (500 MHz, CDCl3) δ: 7.41-7.38 (2H, m), 7.30 (2H, dd, J=8.6, 5.2 Hz), 7.27-7.24 (3H, m), 6.99 (2H, t, J=8.6 Hz), 5.24 (2H, s), 4.52 (2H, q, J=7.0 Hz), 4.13 (2H, s), 3.47 (3H, s), 1.44 (3H, t, J=7.0 Hz). HRMS (M+H) calcd for C23H22N4O4F: 437.1625. found: 437.4719. Anal calcd for C23H21N4O4F: C, 63.29; H, 4.85; N, 12.83. found: C, 62.76; H, 4.84; N, 12.81.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (10 mL), sat. NaHCO3 (10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown residue
  7. customThis residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-9daf4ad7a49a48eba158af96697a3fa2
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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