Diisopropylethylamine → HCID 58458927, compound

HRID 390340Notes

Reaction equation

HRID 390340 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:11][C:10]=1[C:23]([OH:25])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](=[NH:37])[NH:35]O)=[CH:29][CH:28]=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>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOCC>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[N:11][C:10]=1[C:23]1[O:25][N:37]=[C:34]([CH2:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)[N:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

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 21891236HCID 21891236, compoundHCID 178510821HCID 178510821, compound

Product 1

HCID 58458927HCID 58458927, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(benzyloxy)-1-methyl-2-morpholino-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid (prepared according to the procedure in WO2004062613 (0.35 g, 1 mmol), 2-(4-fluorophenyl)-N-hydroxyacetimidamide (0.25, 1.5 mmol) HATU (0.76 g, 2 mmol), DIEA (0.35 mL) and DMAP (10 mg) in 1,4-dioxane (5 mL) was heated at 110° C. for 5 h. The mixture was cooled, diluted with Et2O (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 1:1 hexanes/EtOAc as eluant to afford the title compound (0.24 g, 50% yield) as a white solid. 1HNMR (500 MHz, CDCl3) δ: 7.42-7.39 (2H, m), 7.32 (2H, dd, J=8.4, 5.4 Hz), 7.28-7.25 (3H, m), 7.00 (2H, t, J=8.6 Hz), 5.28 (2H, s), 4.14 (2H, s), 3.84-3.82 (4H, m), 3.55 (3H, s), 3.24-3.22 (4H, m). HRMS (M+H) calcd for C25H25N5O4F: 478.1491. found: 478.5663.

Workup

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

Sources & evidence

ORD record
ord-87ebdf5931644e678aa607fab322a15c
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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