Toluene → HCID 58388020, compound

HRID 2080265Notes

Reaction equation

HRID 2080265 reaction equation
[NH2:1][C:2]1[N:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=S.C1(C)C=CC=CC=1.C(Br)C1C=CC=CC=1.[N:41]#[C:42][NH2:43]>C(#N)C.O.FC(F)(F)C(O)=O.CN1CCCC1=O>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][NH:6][C:4]2[C:3]3[CH:22]=[CH:23][CH:24]=[N:25][C:2]=3[N:1]=[C:42]([NH2:43])[N:41]=2)=[CH:9][CH:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7498Benzyl BromideHCID 9864CyanamideHCID 23130540HCID 23130540, compound

Product 1

HCID 58388020HCID 58388020, compoundYield 4.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-amino-N-(4-benzyloxy-benzyl)-thionicotinamide described in Example A-22 (30 mg, 0.083 mmol) and toluene (1 mL) was added benzyl bromide (0.044 mL, 0.37 mmol), and the solution was refluxed for 3 hours. After cooling, the solvent was evaporated in vacuo, and the residue was washed with diethyl ether twice. A mixture of a portion (13 mg) of the resulting crude product (33 mg), cyanamide (20 mg, 0.48 mmol) and N-methylpyrrolidinone (1 mL) was stirred for 2 hours at 120° C. After cooling, the reaction solution was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and ditrifluoroacetic acid salt of the title compound (0.75 mg, 0.0013 mmol, 4.2%) was obtained.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. washthe residue was washed with diethyl ether twice
  5. temperatureAfter cooling

Sources & evidence

ORD record
ord-11d541e637c144db9af3cb684abad5c2
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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