HCID 67484508, compound → HCID 86626711, compound

HRID 503214Notes

Reaction equation

HRID 503214 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=3[N+:27]([O-])=O)[CH:13]=[CH:14][CH:15]=2)=[N:5][CH:4]=[N:3]1.[H][H]>C(O)C.O=[Pt]=O>[CH3:1][N:2]1[C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17]3[C:18]([NH2:27])=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=3)[CH:13]=[CH:14][CH:15]=2)=[N:5][CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 67484508HCID 67484508, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86626711HCID 86626711, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of 19a (0.6 g, 1.5 mmol) in ethanol (20 ml) was added platinium oxide (0.15 g) and the resultant mixture was hydrogenated at ambient pressure until the hydrogen uptake had ceased. Filtration through celite and concentration of the filtrate in vacuo left 20a, which was taken directly into the next step. The following compounds were prepared in analogy herewith: N1-[3-(2-Ethyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-4-trifluoromethyl-benzene-1,2-diamine (20b) from 19b 4-Methyl-N1-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-benzene-1,2-diamine (20c) from 19c 1-{3-Amino-4-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenylamino]-phenyl}-ethanone (20d) from 19d

Workup

  1. filtrationFiltration through celite and concentration of the filtrate in vacuo
  2. waitleft 20a, which
  3. customThe following compounds were prepared in analogy herewith: N1-[3-(2-Ethyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-4-trifluoromethyl-benzene-1,2-diamine (20b) from 19b 4-Methyl-N1-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-benzene-1,2-diamine (20c) from 19c 1-{3-Amino-4-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenylamino]-phenyl}-ethanone (20d) from 19d

Sources & evidence

ORD record
ord-0b699f2f53614ad2982729e61be19059
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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