Hydrochloric Acid → 1421923-73-0

HRID 1500358Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([NH:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:32]>CCOCC.O1CCOCC1>[ClH:32].[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([NH:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:21])[N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A 500-mL, 3-necked, round-bottomed flask was charged with a solution of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-N′-(pyridin-2-yl)acrylohydrazide (5.5 g) in Et2O (250 mL). The solution was cooled to 5° C., treated with HCl in 1,4-dioxane, allowed to warm to RT and stirred until completion, as shown by TLC analysis (about 1 h). The solids were filtered on a Buchner funnel, washed with Et2O and dried under vacuum to afford 5.5 g (yield: 92%) (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-N′-(pyridin-2-yl)acrylohydrazide hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ, 11.26 (s, 1H), 10.89 (s, 1H), 9.55 (s, 1H), 8.52 (s, 2H), 8.28 (s, 1H), 8.03-8.07 (m, 2H), 7.62-7.59 (d, J=10.4 Hz, 1H), 7.21-7.24 (m, 1H), 7.05-7.09 (m, 1H), 6.16-6.19 (d, J=10.4 Hz, 1H), LCMS for C18H13F6N6O [M+H]+ 443.33; found 443.44 (RT 3.54 min, purity: 99.0%).

Workup

temperatureto warm to RT
customas shown by TLC analysis (about 1 h)
filtrationThe solids were filtered on a Buchner funnel
washwashed with Et2O
customdried under vacuum

Sources & evidence

ORD record: ord-926d1f9cdf904c3c8be363bde3d8d046
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206158B2

Reaction notes

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