Diisopropylethylamine → N-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamide

HRID 240869Notes

Reaction equation

HRID 240869 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:32]=[C:33]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=2)[C:34]([O-:36])=O)[CH2:27][CH2:26]1.[NH2:44][C:45]1[CH:46]=[C:47]([C:51]2[CH:59]=[C:58]3[C:54]([C:55]([C:68]4[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=4)=[CH:56][N:57]3[C:60]3[N:65]=[CH:64][N:63]=[C:62]([NH:66][CH3:67])[CH:61]=3)=[CH:53][CH:52]=2)[CH:48]=[CH:49][CH:50]=1.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([C:55]2[C:54]3[C:58](=[CH:59][C:51]([C:47]4[CH:46]=[C:45]([NH:44][C:34](=[O:36])[C:33]5[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=[C:31]([N:28]6[CH2:27][CH2:26][O:25][CH2:30][CH2:29]6)[CH:32]=5)[CH:50]=[CH:49][CH:48]=4)=[CH:52][CH:53]=3)[N:57]([C:60]3[CH:61]=[C:62]([NH:66][CH3:67])[N:63]=[CH:64][N:65]=3)[CH:56]=2)=[CH:73][CH:72]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 509920026-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineHCID 866513803-Morpholino-5-(trifluoromethyl)benzoate

Product 1

HCID 50992088N-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HATU (100 mg, 0.260 mmol) was added to a mixture solution of 3-morpholino-5-(trifluoromethyl)benzoate (54 mg, 0.195 mmol), 6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (55 mg, 0.130 mmol) and DIPEA (45 μL, 0.26 mmol) in THF (2 mL) at room temperature. 12 hours later, the mixture was added to saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. The collected organic layer was washed with brine and then concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative HPLC). The target compound was obtained as yellow solid.

Workup

  1. extractionextracted with methylene chloride
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe residue was purified by chromatography (preparative HPLC)
  6. customThe target compound was obtained as yellow solid

Sources & evidence

ORD record
ord-64fe5ee48ea34706a4503978114c612f
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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