Benzene → HCID 86607940, compound

HRID 2105010Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([O:24][CH2:25][CH3:26])[CH:15]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].[CH:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C=[N:37][C:36]2[N:39](O)N=NC=2C=1.CC(C)N=C=NC(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:22])[CH3:23])=[C:16]([O:24][CH2:25][CH3:26])[CH:15]=2)[C:11]([O:13][N:37]=[C:36]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH2:39])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2-(4-cyanophenylamino)-2-(3-ethoxy-4-isopropoxyphenyl)acetic acid (US2004242585, which is incorporated herein by reference) (525 mg, 1.48 mg) and benzene amideoxime (242 mg, 1.78 mmol) in 10 mL CH2Cl2/DMF (9:1) at 0° C., were added HOAt (242 mg, 1.78 mmol), DIC (0.279 mL, 1.78 mmol) and TEA (0.248 mL, 1.78 mmol). The mixture was stirred at 0° C. for 15 min, then at rt for 6 h. The mixture was diluted with EtOAc, washed with H2O, 1 N HCl, H2O, sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 700 mg of Intermediate 187.1 as a white solid.

Workup

customat 0° C.
waitat rt for 6 h
washwashed with H2O, 1 N HCl, H2O, sat. NaHCO3 and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record: ord-7a89d4e26c934289b96b0c6757958804
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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