Hydrazine hydrate (1:1) → 1-[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-4-(trifluoromethyl)pyridin-3-yl]methanamine

HRID 2206918Notes

Reaction equation

[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]2([C:40]([F:43])([F:42])[F:41])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][N:25]4C(=O)C5C(=CC=CC=5)C4=O)=[C:20]([C:36]([F:39])([F:38])[F:37])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.NN>C(O)C>[F:45][C:2]([F:1])([F:44])[C:3]1[CH:4]=[C:5]([C:13]2([C:40]([F:41])([F:42])[F:43])[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([CH2:24][NH2:25])=[C:20]([C:36]([F:37])([F:38])[F:39])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-{[6-{3-[3,5-Bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-4-(trifluoro-methyl)pyridin-3-yl]methyl}-1H-isoindole-1,3(2H)-dione (0.31 g) and hydrazine hydrate (0.035 ml) were added to ethanol (5 ml), and heated at 80° C. for 5 hours. The solvent was distilled off under reduced pressure, and then t-butyl methyl ether was added. The undissolved matters were removed by filtration, and the target compound (0.24 g) was obtained after concentration under reduced pressure.

Workup

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

Sources & evidence

ORD record: ord-76cd7067138f4bf3bb5c04dfd6e232de
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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