Hydrochloric Acid → HCID 71263595, compound

HRID 2272299Notes

Reaction equation

HRID 2272299 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([B:35]4[O:39]C(C)(C)C(C)(C)[O:36]4)[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.C1(B(O)O)C=CC=CC=1.Cl>O1CCCC1>[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:30]=[C:31]([B:35]([OH:36])[OH:39])[CH:32]=[CH:33][CH:34]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19](=[O:20])[NH:21][CH3:22])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 131732263HCID 131732263, compound

Product 1

HCID 71263595HCID 71263595, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)benzofuran-3-carboxamide (269 mg, 0.45 mmol), polymer-supported benzeneboronic acid (770 mg, 2.23 mmol), aqueous 5N HCl (0.62 mL, 3.12 mmol) in tetrahydrofuran (15 mL) was stirred at room temperature for 48 hours. The mixture was filtered, the filtrate was concentrated to dryness and purified by reverse phase HPLC to afford 3-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)phenylboronic acid (41 mg, 0.078 mmol, 17% yield) as a white solid. 1H NMR (METHANOL-d4) δ 7.99-7.95 (m, 2H), 7.94 (s, 1H), 7.77-7.38 (m, 4H), 7.32-7.25 (m, 3H), 3.32 (s, 3H), 2.98 (s, 3H), 2.29-2.25 (m, 1H), 1.10-0.37 (m, 4H). LCMS (m/z, ES+)=523 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-511a413f51944b5fbf3fa55a02976f80
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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