HCID 67484829, compound → HCID 67484626, compound

HRID 503213Notes

Reaction equation

HRID 503213 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][O:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24](F)(F)F)=[CH:20][C:19]=3[N+:28]([O-:30])=[O:29])[CH:14]=[CH:15][CH:16]=2)=[N:6][CH:5]=[N:4]1)C.C(C(OCC1NC=CN=1)C1C=C(N)C=CC=1)C>>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][O:9][CH2:8][C:7]3[N:3]([CH3:1])[N:4]=[CH:5][N:6]=3)[CH:12]=2)=[C:19]([N+:28]([O-:30])=[O:29])[CH:20]=1

Participants

3

Reactant 2

HCID 67484829HCID 67484829, compoundHCID 67484897HCID 67484897, compound

Product 1

HCID 67484626HCID 67484626, compoundYield 78%

Procedure

To a solution of compound 18a (1.0 g, 4.9 mmol) in anhydrous NMP (10 ml) was added triethylamine (0.68 ml, 4.9 mmol) and compound 17a (0.68 ml, 4.91 mmol) and the resultant mixture was stirred at 100° C. over night. The cooled reaction mixture was poured into ice-water and the precipitate was filtered off, re-dissolved in dichloromethane, dried over magnesium sulphate and concentrated in vacuo. This concentrate was triturated in a mixture of diethyl ether and petroleum ether to afford 19a as a brownish solid (1.2 g, 62%). The following compounds were prepared in analogy herewith: [3-(2-Ethyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-(2-nitro-4-trifluoromethylphenyl)-amine (19b) from 17a and 18b. Yield: 78% (4-Methyl-2-nitro-phenyl)-[3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenyl]-amine (19c) from 17b and 18a. Yield: 20% 1-{4-[3-(2-Methyl-2H-[1,2,4]triazol-3-ylmethoxymethyl)-phenylamino]-3-nitro-phenyl}-ethanone (19d) from 17c and 18a. Yield: 74%

Sources & evidence

ORD record
ord-8d2f74e11fa04e57b283fb72ecd39140
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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