Triethylamine → HCID 23533346, compound

HRID 2414515Notes

Reaction equation

HRID 2414515 reaction equation
CN1CCN(C2C=C[C:11]3[C:12](C=2)=[CH:13][CH:14]=[C:15]2[C:20]=3[O:19][C:18]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)=[O:22])=[CH:17][C:16]2=[O:36])CC1.C1C=CC2N(O)N=NC=2C=1.CN([C:51]([O:55]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:70]([N:72]([CH2:75]C)[CH2:73][CH3:74])[CH3:71].COC1C=C([N:85]2CCOCC2)C=CC=1N>CN(C)C1C=CN=CC=1.CN(C)C=O.C(OCC)(=O)C>[CH3:51][O:55][C:29]1[CH:28]=[C:27]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[CH:26]=[CH:25][C:24]=1[NH:23][C:21]([C:18]1[O:19][C:20]2[C:15]([C:16](=[O:36])[CH:17]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[N:85]1[CH2:74][CH2:73][N:72]([CH3:75])[CH2:70][CH2:71]1)=[O:22]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 4149602-Methoxy-4-morpholinoanilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69272428HCID 69272428, compound

Product 1

HCID 23533346HCID 23533346, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) (9.10 g, 0.35 mmol), HOBt (0.10 g, 0.7 mmol), TBTU (0.225 g, 0.7 mmol), 4-(dimethylamino)pyridine (0.01 g, catalytic amount), triethylamine (0.15 mL, 1.04 mmol), and commercially available 2-methoxy-4-morpholin-4-yl-phenylamine (SALOR) (0.08 g, 0.38 mmol) were dissolved in dimethylformamide (2.5 mL) and stirred at room temperature overnight. Ethyl acetate (150 mL) was added and the resulting mixture was washed with water (3×50 mL), dried (Na2SO4), filtered, concentrated under vacuum and triturated with ether to yield a yellow solid (85 mg, 54%). LCMS: m/z=480.3.

Workup

  1. washthe resulting mixture was washed with water (3×50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customtriturated with ether

Sources & evidence

ORD record
ord-a33e34d9be1d4ffe8663b4afbcfc7026
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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