Toluene → N-(2-methoxyethyl)-4-methyl-2-({1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}methyl)-2H-indazol-5-carboxamide

HRID 2174924Notes

Reaction equation

HRID 2174924 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8].[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:30][CH:31]=4)[CH2:23][CH2:24]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 89601954HCID 89601954, compound

Product 1

HCID 71581864N-(2-methoxyethyl)-4-methyl-2-({1-[4-(trifluoromethoxy)benzoyl]piperidin-4-yl}methyl)-2H-indazol-5-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

150 mg of the amine prepared in Example 1a were first dissolved in 1.5 ml pyridine. 101 mg of 4-(trifluoromethoxy)benzoyl chloride were then added and the mixture stirred for 30 min at RT. The reaction mixture was then treated with some toluene and concentrated. The residue was taken up in ethyl acetate and washed twice with water, twice with saturated sodium hydrogen carbonate solution (pH 9) and once with saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 118.2 mg of the title compound.

Workup

  1. concentrationconcentrated
  2. washwashed twice with water, twice with saturated sodium hydrogen carbonate solution (pH 9) and once with saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified chromatographically on the Biotage SP4

Sources & evidence

ORD record
ord-aff89784a16c4753b2ee553f28aa8cb6
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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