4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide → HCID 178489626, compound

HRID 412721Notes

Reaction equation

[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]([CH:9]([CH3:15])[C:10](OCC)=O)=[N:8][C:4]=2[CH:3]=1.[NH2:18][C:19]1[CH:38]=[CH:37][C:22]([C:23]([NH:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[O:24])=[CH:21][C:20]=1[NH:39][CH3:40]>CN1CCCN(C)C1=O>[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]([CH:9]([C:10]3[N:39]([CH3:40])[C:20]4[CH:21]=[C:22]([C:23]([NH:25][CH2:26][CH2:27][O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[O:35][CH3:36])=[O:24])[CH:37]=[CH:38][C:19]=4[N:18]=3)[CH3:15])=[N:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture comprising ethyl 2-(5-hydroxy-1H-benzoimidazol-2-yl)propionate (148 mg, 0.63 mmol), 4-amino-N-[2-(2-methoxyphenoxy)ethyl]-3-methylaminobenzamide (200 mg, 0.63 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (0.5 mL) was stirred at room temperature until homogeneous, degassed under vacuum and concentrated by heating at 170° C. for 2 hours under a stream of N2. The residue was cooled to room temperature and rinsed with an excess of ethyl ether. The resulting amorphous material was taken up in 50% aqueous acetonitrile and purified by preparative reverse phase HPLC (2-50% CH3CN/H2O) to provide 2-[1-(5-hydroxy-1H-benzoimidazol-2-yl)ethyl]-N-[2-(2-methoxyphenoxy)ethyl]-3-methyl-3H-benzoimidazole-5-carboxamide (40 mg, 13% yield) as a light pink solid; MS (BioIon) C27H27N5O4 m/e calc 485.59; found 486.5 (MH+).

Workup

customdegassed under vacuum
concentrationconcentrated
temperatureThe residue was cooled to room temperature
washrinsed with an excess of ethyl ether
custompurified by preparative reverse phase HPLC (2-50% CH3CN/H2O)

Sources & evidence

ORD record: ord-854051ec7b7648a6bf63270c0d152113
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562854B2

Reaction notes

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