Triethylamine → HCID 136173632, compound

HRID 1161453Notes

Reaction equation

HRID 1161453 reaction equation
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[NH2:3].C(N(CC)CC)C.C[O:21][C:22](=O)[N:23]=[C:24](SC)[C:25](=[N:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[C:39]([F:45])[CH:38]=1)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1>CN(C=O)C>[C:43]([C:40]1[CH:41]=[CH:42][C:37]([NH:36][CH:25]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[C:24]2[NH:23][C:22](=[O:21])[N:2]([C:4]3[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=3[C:6]([OH:8])=[O:7])[N:3]=2)=[CH:38][C:39]=1[F:45])#[N:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 72312782HCID 72312782, compound

Product 1

HCID 136173632HCID 136173632, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

After adding 55 mg of 2-hydrazinobenzoic acid hydrochloride and 101 μl of triethylamine to a solution of 120 mg of [2-(4-cyano-3-fluorophenylimino)-2-(3,4-dimethoxyphenyl)-1-methylsulfanylethylidene]carbamic acid methyl ester in 3 ml of DMF, the mixture was stirred at 85° C. for 16 hours under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 3 ml of a methanol:THF=1:1 mixed solvent. After adding 58 μl of acetic acid and 91 mg of sodium cyanotrihydroborate to the solution, the mixture was stirred at room temperature for 15 hours. Ethyl acetate was then added to the reaction mixture. The organic layer was washed with dilute hydrochloric acid and saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give the title compound (100 mg) as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 3 ml of a methanol
  3. additionAfter adding 58 μl of acetic acid and 91 mg of sodium cyanotrihydroborate to the solution
  4. stirringthe mixture was stirred at room temperature for 15 hours
  5. additionEthyl acetate was then added to the reaction mixture
  6. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccating agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-1defcdb2d277416c9c1834c799fbc5a6
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…