Triethylamine → HCID 59353026, compound

HRID 1914686Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.C(N(CC)CC)C.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl.C1COCC1.O>[CH3:14][O:13][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)[C:7]([N:30]1[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]1)=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Nitro-5-methoxybenzoic acid (1 g; 5.07 mmol; 1 eq; commercially available IMPAMEX) is dissolved in a mixture of DCM (40 mL) and THF (10 mL) at room temperature. It is then cooled down at 0° C. and thionyl dichloride (1.1 mL; 15.22 mmol; 3 eq) is added slowly. After 30 min, triethylamine (2.11 mL; 15.22 mmol; 3 eq) and 1-methylpiperazine (1.64 mL; 15.22 mmol; 3 eq) are added at 0° C. and the reaction mixture is gently warmed up to rt and stirred for 48 h. Water is added and the solvents are evaporated. The product is extracted with EtOAc and the organic phase is washed with aqueous Na2CO3 and dried over MgSO4. The solvent is concentrated under reduced pressure to afford 900 mg (63.5%) of the title compound. The next step is carried out directly on the crude material. LC/MS: (ES+): 280.3; (ES−): 278.5

Workup

temperaturethe reaction mixture is gently warmed up to rt
customthe solvents are evaporated
extractionThe product is extracted with EtOAc
washthe organic phase is washed with aqueous Na2CO3
dry with materialdried over MgSO4
concentrationThe solvent is concentrated under reduced pressure

Sources & evidence

ORD record: ord-02e49fd171c047178f3c02816a64efaa
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614215B2

Reaction notes

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