Triethylamine → Methyl 4-((2-(isopropylcarbamoyl)-4-phenoxyphenyl)carbamoyl)benzoate

HRID 2099967Notes

Reaction equation

[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][C:3]=1[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=[O:5].[CH3:21][O:22][C:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)=[O:24].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:7]([NH:6][C:4]([C:3]1[CH:10]=[C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][C:2]=1[NH:1][C:29]([C:28]1[CH:32]=[CH:33][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:26][CH:27]=1)=[O:30])=[O:5])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 34C (72 mg, 0.27 mmol) in DMF (4 mL) was treated with 4-(methoxycarbonyl)benzoic acid (78 mg, 0.43 mmol), HOBt (66 mg, 0.43 mmol) and triethylamine (100 mg, 1.0 mmol). The solution was treated with EDCI (96 mg, 0.5 mmol) at room temperature for 15 minutes, and then warmed to 65° C. for 16 hours. The reaction mixture was partitioned between EtOAc (20 mL) and 1 M HCl (20 mL). The organic layer was washed with 1 N HCl (20 mL), 1 N NaOH (20 mL) and brine (20 mL). The reaction was dried (Na2SO4), filtered, and concentrated to a solid. The crude material was purified by chromatography (SiO2, 1:2 EtOAc in heptane) to afford 34D (99 mg, 85%).

Workup

customThe reaction mixture was partitioned between EtOAc (20 mL) and 1 M HCl (20 mL)
washThe organic layer was washed with 1 N HCl (20 mL), 1 N NaOH (20 mL) and brine (20 mL)
dry with materialThe reaction was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated to a solid
customThe crude material was purified by chromatography (SiO2, 1:2 EtOAc in heptane)

Sources & evidence

ORD record: ord-939636c2a5a84e6ab04a867776e6bd59
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569725B2

Reaction notes

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