Trifluoroacetic acid → HCID 66634251, compound

HRID 1925154Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:18]=[N:17][C:16]([NH:19]CC4C=CC(OC)=CC=4OC)=[CH:15][CH:14]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1.C1(OC)C=CC=CC=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:18]=[N:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1.[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[N:18]=[N:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH3:12])=[N:9][N:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine (750 mg, 1.598 mmol), anisole (0.349 mL, 3.20 mmol), and TFA (1.0 mL, 12.98 mmol) in DCM (5.0 mL) was heated in a microwave on high absorbance for 2 hrs at 75° C. The reaction was stripped to dryness via rotary evaporation, and the resulting oil was treated with Et2O to produce a solid. The solid was filtered and dried under vacuum to provide the title compound, 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)pyridazin-3-amine 2,2,2-trifluoroacetate (400 mg, 0.923 mmol, 57.8% yield) as a yellow solid. 1H NMR 48F (400 MHz, DMSO-d6) δ ppm 1.77 (d, J=7.07 Hz, 3 H) 5.05 (d, J=7.07 Hz, 1 H) 7.44 (d, J=9.60 Hz, 1 H) 7.50 (dd, J=9.73, 1.64 Hz, 1 H) 7.73-7.84 (m, 1 H) 7.92 (d, J=9.60 Hz, 1 H) 8.56 (br. s., 2 H) 8.81 (s, 1 H). ESI-MS:m/z 319.1 (M+H)+.

Workup

customThe reaction was stripped to dryness via rotary evaporation
additionthe resulting oil was treated with Et2O
customto produce a solid
filtrationThe solid was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-f6472f1e72d54578acd33cf93dac1448
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178534B2

Reaction notes

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