Hydrazine hydrate (1:1) → 1-{2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidin-5-yl}methanamine

HRID 2206912Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:37]([F:40])([F:39])[F:38])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH2:25][N:26]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:17][N:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].O.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:37]([F:38])([F:39])[F:40])[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[C:18]([CH2:25][NH2:26])=[CH:17][N:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

2-({2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (2.35 g) was added to ethanol (50 ml), followed by addition of hydrazine hydrate (0.37 ml) at room temperature. The reaction mixture was heated at 80° C. for 6 hours. The solvent was distilled off under reduced pressure, and then t-butyl methyl ether was added. The undissolved solids were removed by filtration, and the target compound was (1.71 g) obtained as a crude product after concentration under reduced pressure.

Workup

distillationThe solvent was distilled off under reduced pressure
additiont-butyl methyl ether was added
customThe undissolved solids were removed by filtration

Sources & evidence

ORD record: ord-f51f455c79e44a4ea9db58da284838a7
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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