Trifluoroacetic acid → HCID 89961656, compound

HRID 1521577Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=S)[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1.[F:19][C:20]([F:26])([F:25])[C:21]([NH:23][NH2:24])=O.C1(O)CCCCC1.FC(F)(F)C(O)=O>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[N:16]4[C:21]([C:20]([F:26])([F:25])[F:19])=[N:23][N:24]=[C:15]4[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A flask containing the title compound from Example 2 Step E (9.0 mg, 0.04 mmol), 2,2,2-trifluoroacetohydrazide (3.2 mg, 0.04 mmol) and cyclohexanol (0.50 mL) was heated at 120° C. overnight. The reaction was then concentrated to give a residue that was diluted with dimethylsulfoxide, acidified with trifluoroacetic acid, and passed through a syringe filter before being purified by reverse phase HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid). Fractions containing product were combined, 1 M hydrochloric acid was added, and the solution concentrated to provide the title compound: LCMS m/z 330.99 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.09 (br s, 1H), 8.76 (br s, 1H), 8.26 (d, J=Hz, 1H), 7.75-7.59 (m, 4H), 3.34 (br s, 1H), 2.90-2.85 (m, 1H), 2.52-2.40 (m, 3H), 2.27 (br s, 1H).

Workup

concentrationThe reaction was then concentrated
customto give a residue that
custompassed through a syringe
filtrationfilter
custombefore being purified by reverse phase HPLC (C18 column, 10 to 100% acetonitrile/water
additionFractions containing product
addition1 M hydrochloric acid was added
concentrationthe solution concentrated

Sources & evidence

ORD record: ord-47b94a4c01cb4abb9b14fd64f570a219
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

Loading…