Boron tribromide → HCID 59559615, compound

HRID 1177915Notes

Reaction equation

[Br:1][C:2]1[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[CH2:13][NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[O:16])[CH2:8][CH2:7]1)=[O:5].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[CH2:13][NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[O:16])[CH2:8][CH2:7]1)=[O:5]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of Biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide (prepared by the method as described above) (115 mg, 0.21 mmol) in DCM (5 ml) was cooled to −78° C. To the resulting mixture added BBr3 (357 mg, 1.42 ml, 1.43 mmol) and stirred at same temperature for 4 hrs. The reaction mixture was brought to −30° C. and quenched with cold MeOH dropwise, concentrated the mixture under reduced pressure to get the residue. The obtained residue was purified by preparative HPLC to afford 33 mg (29.5% yield) Biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-hydroxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 98.95%. 1H NMR (DMSO-d6): δ 10.1 (s, 1H), 8.7-8.6 (bs, 1H), 8.0-7.9 (d, 2H), 7.8-7.7 (dd, 4H), 7.5-7.4 (m, 4H), 6.8-6.7 (t, 2H), 4.24-4.1 (dd, 2H), 3.74-3.44 (m, 6H), 3.24-3.1 (bd, 2H).

Workup

customwas brought to −30° C.
customquenched with cold MeOH dropwise
concentrationconcentrated the mixture under reduced pressure
customto get the residue
customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-7ae813790dbd4047b469ceb541f6903a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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