Nitrogen → HCID 16004686, compound

HRID 1256682Notes

Reaction equation

N#N.C[O:4][C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[C:7]([O:13]C)[C:6]=1[CH2:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23])=[O:17].B(Br)(Br)Br>C(Cl)Cl>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:13])[C:6]=1[CH2:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23])=[O:17]

Participants

Conditions

Temperature: -78 °C

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid (17) (134 mg, 0.39 mmol) in anhydrous DCM (5.3 mL), cool the solution to −78° C. and add dropwise BBr3 (240 μL, 2.55 mmol). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 2 h at rt. Add dropwise ice water, separate layers and extract aqu. layer with EtOAc (3 times). Wash combined organic layer with brine and dry with Na2SO4. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 3-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18) (29 mg, 22%) as a yellowish solid. 1H NMR (400 MHz, CD3OD): 3.69 (s, 2H); 5.97 (s, 2H); 7.43 (t, 1H, J=8.0 Hz); 7.76 (br.dd, 1H, J1=7.6 Hz); 7.84 (br.dd, 1H, J1=8.1 Hz); 8.17 (t, 1H, J=1.8 Hz).

Workup

custom(The following reaction
temperatureafter slowly warming up for additional 2 h at rt
customseparate layers
extractionextract aqu
washWash
dry with materialdry with Na2SO4
customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

Sources & evidence

ORD record: ord-a0d2500cedd84c18b6f7acfa23491243
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461207B2

Reaction notes

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