Trifluoroacetic acid → HCID 89401945, compound

HRID 1486994Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[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[CH2:35][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:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:11][C:9]([F:10])([F:12])[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[CH2:35][C:24]4([CH2:27][NH:26][CH2:25]4)[CH2:23]3)=[O:21])[N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:37])[F:36])[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[3.3]heptane-2-carboxylate (0.13 g) was dissolved in DCM (1.5 mL). The reaction mixture was cooled to 0° C. and CF3COOH (1.5 mL) was added. The reaction mixture was allowed to warm to room temp. where it was stirred for 4 h. The reaction mixture was concentrated under reduced pressure (35° C., 20 mmHg) to afford 0.100 g of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-1-(2,6-diazaspiro[3.3]heptan-2-yl)prop-2-en-1-one 2,2,2-trifluoroacetate (Yield 95.23%). 1H NMR (400 MHz, DMSO) δ 9.49 (s, 1H), 8.52-8.5 (m, 3H), 8.32 (s, 1H), 7.44-7.42 (d, 1H, J=10.4 Hz), 5.97-5.94 (d, J=10.4 Hz, 1H), 4.37-3.93 (m, 8H); LCMS calcd for C18H16F6N5O [M+H]+ 432.34. found 432.29 at retention time 2.256 min.

Workup

temperatureto warm to room temp. where it
concentrationThe reaction mixture was concentrated under reduced pressure (35° C., 20 mmHg)

Sources & evidence

ORD record: ord-0c785a3843d64806ac620fb6d325a1ca
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428490B2

Reaction notes

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