(E)-4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine → 4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine

HRID 77478Notes

Reaction equation

HRID 77478 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[N:19]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1>C(OCC)(=O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=4)[N:19]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 1

HCID 86679767(E)-4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine

Product 1

HCID 866797684-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amineYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)vinyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine (0.03 g, 0.064 mmol) in ethyl acetate (3 mL), Pd—C (0.014 g, 0.129 mmol) was added and the reaction mixture was stirred at room temperature under H2 overnight. The reaction mixture was filtered through a pad of celite, washed with ethyl acetate, and concentrated to get 4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine as a yellow gum (0.03 g, 75% yield). LCMS: R.T.=1.06 min; [M+H]+=469.27.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf6be84cbd94ff2abc8ebfc017b7310
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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