Trifluoroacetic acid → HCID 122504722, compound

HRID 1487006Notes

Reaction equation

[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([N:22]3[CH2:36][CH2:35][C:24]4([CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)[CH2:23]3)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[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]([N:22]3[CH2:36][CH2:35][C:24]4([CH2:25][NH:26][CH2:27]4)[CH2:23]3)=[O:21])[N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:38])[F:37])[CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(Z)-tert-Butyl 6-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)-2,6-diazaspiro[3.4]octane-2-carboxylate (0.05 g) was dissolved in DCM (20 mL), cooled to 0° C. and CF3COOH (0.5 mL) was added. The reaction mixture was stirred at room temperature for 4 h, concentrated under reduced pressure (35° C., 20 mmHg) to give (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-1-(2,6-diazaspiro[3.4]octan-6-yl)prop-2-en-1-one 2,2,2-trifluoroacetate (0.03 g, 95% yield). 1H NMR (400 MHz, DMSO) δ=9.25 (s, 1H), 8.77 (brs, 1H), 8.59 (s, 2H), 8.30 (s, 1H), 7.39-7.37 (d, 1H, J=10.4 Hz), 6.15-6.12 (d, J=10.4 Hz, 1H), 3.86-3.65 (brs, 4H), 2.14 (s, 2H), 1.49 (s, 2H), 0.85-1.23 (m, 2H); LCMS calcd. for C19H18F6N5O [M+H]+ 446.36. found 446.12 at retention time 2.161 min.

Workup

concentrationconcentrated under reduced pressure (35° C., 20 mmHg)

Sources & evidence

ORD record: ord-38827e6b677c4e55bd5d91cb4791cb13
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428490B2

Reaction notes

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