Sodium Carbonate → 1-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678434Notes

Reaction equation

HRID 1678434 reaction equation
O1[CH2:6][CH2:5][O:4][CH2:3]C1.Cl[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[O:23])[CH2:18][CH2:17]2)[N:9]=1.[CH3:36][C:37]1C=CC=[CH:39][C:38]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CC#N>[CH3:15][NH:14][C:12]1[N:13]=[C:8]([C:37]2[CH:36]=[CH:6][C:5]([O:4][CH3:3])=[CH:39][CH:38]=2)[N:9]=[C:10]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:33])([F:35])[F:34])=[O:23])[CH2:20][CH2:21]2)[N:11]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27332672-Methylphenyl boronic acidHCID 866443121-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide2×

Product 1

HCID 594477541-{4-(Methylamino)-6-[4-(methoxy)phenyl]-1,3,5-triazin-2-yl}-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, to a 1,4-dioxane (3.0 ml) suspension of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidine carboxamide (Intermediate 7d, 75 mg, 0.17 mmol, 1.0 equiv) was added (2-methylphenyl)boronic acid (29 mg, 0.21 mmol, 1.2 equiv), Na2CO3 (37 mg, 0.35 mmol, 2.0 equiv) in 3:1 CH3CN:H2O, and lastly Pd(PPh3)4 (10 mg, 0.0088 mmol, 0.05 equiv). The reaction mixture was heated at 150° C. for 25 minutes. The resulting suspension was diluted with ethyl acetate (10 ml), washed with water (5 ml), dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in 2.0 ml DMSO and purified via reverse-phase HPLC purification to afford the title compound. MS (ES+): m/e 501.0 [M+H]+.

Workup

  1. washwashed with water (5 ml)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified via reverse-phase HPLC purification

Sources & evidence

ORD record
ord-aa55639da5b7455fa0b541556a26e5e9
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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