Toluene → HCID 178512316, compound

HRID 2080241Notes

Reaction equation

HRID 2080241 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=S)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(Br)C1C=CC=CC=1.[N:44]#[C:45][NH2:46]>C(#N)C.O.FC(F)(F)C(O)=O.CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[N:46][C:45]#[N:44])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7498Benzyl BromideHCID 9864CyanamideHCID 58875330HCID 58875330, compound

Product 1

HCID 178512316HCID 178512316, compoundYield 4.5%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of quinoline-6-carbothioic acid 4-benzyloxy-benzylamide described in Preparation Example E+-10 (57 mg, 0.15 mmol) and toluene (2 mL) was added benzyl bromide (0.089 mL, 0.74 mmol), which was then stirred under reflux for 90 minutes. After cooling, the solvent was evaporated in vacuo, and the residue was washed with diethyl ether twice. A mixture of a portion (16 mg) of the resulting crude product (72 mg), cyanamide (20 mg, 0.48 mmol) and N-methylpyrrolidinone (1 mL) was stirred for 2.5 hours at 120° C. After cooling, the reaction solution was filtered through a membrane filter, the filtrate was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (0.76 mg, 0.0015 mmol, 4.5%) was obtained.

Workup

  1. temperatureunder reflux for 90 minutes
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. washthe residue was washed with diethyl ether twice
  5. stirringwas stirred for 2.5 hours at 120° C
  6. temperatureAfter cooling
  7. filtrationthe reaction solution was filtered through a membrane
  8. filtrationfilter

Sources & evidence

ORD record
ord-771b2f3a6a984a46a3e368d2ed2a8494
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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