Trifluoroacetic acid → Trifluoroacetic acid

HRID 1521572Notes

Reaction equation

HRID 1521572 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=S)[CH2:11][CH2:10]3)[CH:2]=1.[CH:18]([NH:20][NH2:21])=O.C1(O)CCCCC1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>CS(C)=O>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]2[CH:18]=[N:20][N:21]=[C:12]2[CH2:11][CH2:10]3)[CH:2]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7966CyclohexanolHCID 12229HydrazinecarboxaldehydeHCID 251803006-Pyridin-3-yl-3,4-dihydroquinoline-2(1H)-thione

Product 2

HCID 6422Trifluoroacetic acidHCID 89961879HCID 89961879, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A flask containing the title compound from Example 1 Step B (20 mg, 0.08 mmol), formic hydrazide (6.0 mg, 0.10 mmol) and cyclohexanol (0.50 ml, 0.08 mmol) was heated to reflux for 6 hours. The reaction was cooled to room temperature, diluted with dimethylsulfoxide, acidified with trifluoroacetic acid and passed through a syringe filter. Purification by reverse phase HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) provided the title compound: LCMS m/z 249.16 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 9.90 (s, 1H), 9.30 (d, J=2.0 Hz, 1H), 9.01 (ddd, J=1.5, 1.9, 8.2 Hz, 1H), 8.93 (d, J=5.6 Hz, 1H), 8.23 (dd, J=5.8, 8.2 Hz, 1H), 8.10-8.07 (m, 2H), 8.02 (dd, J=1.9, 8.4 Hz, 1H), 3.46-3.43 (m, 2H), 3.38-3.35 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. custompassed through a syringe
  4. filtrationfilter
  5. customPurification by reverse phase HPLC (C18 column, 10 to 100% acetonitrile/water

Sources & evidence

ORD record
ord-1deea4930217481a8cfcb8f97a856218
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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