Nitrogen → HCID 59819881, compound

HRID 383617Notes

Reaction equation

N#N.COC(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:28])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22]C)[C:19]([O:24]C)=[C:18]([O:26]C)[CH:17]=2)[C:7]=1NC1C=CC=CC=1.B(Br)(Br)Br.[Cl-].[Na+].O.CC[O:46][C:47]([CH3:49])=[O:48]>C(Cl)Cl>[OH:22][C:20]1[CH:21]=[C:16]([CH2:15][CH2:14][C:13]([NH:12][C:8]2[CH:7]=[C:6]([NH:12][C:8]3[CH:9]=[C:49]([CH:11]=[CH:6][CH:7]=3)[C:47]([OH:46])=[O:48])[CH:11]=[CH:10][CH:9]=2)=[O:28])[CH:17]=[C:18]([OH:26])[C:19]=1[OH:24]

Participants

Conditions

Temperature: -78 °C

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 3-{3-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-phenylamino-benzoic acid methyl ester (91) (36 mg, 0.08 mmol) in anhydrous DCM (2.3 mL) at −78° C., add dropwise a 1M solution of BBr3 in DCM (930 μL, 0.93 mmol) and stir for additional 30 min at −78° C. After slowly warming up stir the reaction solution for additional 4 h at rt. Cool reaction mixture to 0° C., add dropwise water/THF (1+1) and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 3-{3-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-phenylamino}-benzoic acid (92) (10 mg, 33%) as a white solid. 1H NMR (400 MHz, CD3OD): 2.60 (t, 2H, J=7.7 Hz); 2.85 (t, 2H, J=7.7 Hz); 6.29 (s, 2H); 6.70 (dd, 1H, J1=8.0 Hz, J2=2.0 Hz); 7.06 (d, 1H, J=8.0 Hz), 7.21 (t, 1H, J=8.0 Hz), 7.33-7.37 (m, 2H), 7.45 (mc, 1H); 7.50-7.54 (m, 1H); 7.77 (s, 1H).

Workup

custom(The following reaction
temperatureAfter slowly warming up
stirringstir the reaction solution for additional 4 h at rt
temperatureCool
customreaction mixture to 0° C.
customremove solvent
customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

Sources & evidence

ORD record: ord-2c8fceb87eef4a59b01680de6421f08a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367677B2

Reaction notes

Loading…