Sodium Chloride → HCID 46916973, compound

HRID 592309Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][C:14]([CH:17]([CH3:19])[CH3:18])=[N:13][C:12]=3[CH:11]=[C:10]([C:20](O)=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[Cl-].[Na+].Cl.[CH3:26][C:27]1[N:31]=[C:30]([CH:32]([NH2:34])[CH3:33])[O:29][N:28]=1.CN1CCOCC1.Cl.CN(C)CCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[O:15][C:14]([CH:17]([CH3:19])[CH3:18])=[N:13][C:12]=3[CH:11]=[C:10]([C:20]([NH:34][C@@H:32]([C:30]3[O:29][N:28]=[C:27]([CH3:26])[N:31]=3)[CH3:33])=[O:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7-(4-fluorophenyl)-2-isopropyl-1,3-benzoxazole-5-carboxylic acid with three equivalents of sodium chloride (8.5 mg, 16.0 μmol), R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine hydrochloride (3.35 mg, 17.0 μmol) and N-methylmorpholine (8.8 μL, 0.08 mmol) in N,N-dimethylformamide (0.16 mL) were added N-[2-(dimethylamino)ethyl]-N′-ethylcarbodiimide hydrochloride (5.35 mg, 28.0 μmol), 1-hydroxy-7-azabenzotriazole (1.09 mg, 8.0 μmol). The mixture was stirred at 50° C. for 18 h. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide) gave the title compound (2 mg). HRMS [M+1] found=409.1662. 1H NMR (500 MHz, DMSO-d6): δ 9.23 (1H, m), 8.16 (3H, m), 7.99 (1H, s), 7.37 (2H, m), 5.44, 1H, m), 3.90 (3H, s), 3.44 (1H, m), 2.34 (3H, s), 1.65 (3H, d, J=7.11 Hz), 1.37 (6H, d, J=6.75 Hz).

Workup

customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide)

Sources & evidence

ORD record: ord-6122c68d3b6b4cf09fc8d7788e3190b5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238647B2

Reaction notes

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