Diisopropylethylamine → HCID 90133754, compound

HRID 1051404Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[CH:3]([CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:9]1)[CH2:4][C:5]#[N:6].Cl.[NH2:27][OH:28].CCN(C(C)C)C(C)C>CCO>[F:25][C:2]([F:1])([F:24])[CH:3]([CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)[CH2:9]1)[CH2:4]/[C:5](=[N:27]/[OH:28])/[NH2:6]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 50 mL round-bottomed flask, 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanenitrile (200 mg, 549 μmol) and hydroxylamine hydrochloride (37.9 mg, 549 μmol) were combined with EtOH (2 ml) to give a colorless suspension. DIEA (106 mg, 144 μl, 823 μmol) was added and the resulting mixture was stirred at 100° C. for 6 hr. The crude reaction mixture was concentrated in vacuo to give (Z)-4,4,4-trifluoro-N′-hydroxy-3-((3-(3-(trifluoromethyl)phenyl)-piperidin-1-yl)methyl)butanimidamide as a viscous oil. 85% pure by LC-MS. MH+=398.

Workup

customto give a colorless suspension
customThe crude reaction mixture
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-ede26fb7313946d59ed7e42c9eca6a96
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388172B2

Reaction notes

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