Triethylamine → Methyl 4-chloro-2-[(3,5-dichloropyridin-2-yl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate

HRID 1628494Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])[C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][N:21]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:3]2[N:17]=[C:18]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][N:21]=3)[N:12]([CH2:13][CH2:14][CH2:15][OH:16])[C:4]=2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 4-chloro-3-{[(3,5-dichloropyridin-2-yl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate (3.58 g, 7.73 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.63 g, 8.50 mmol), and triethylamine (1.2 mL) in tetrahydrofuran (30 mL) was stirred at 50° C. for 3 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with tetrahydrofuran/ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether to give the title compound as a colorless powder (3.32 g, 7.73 mmol, 100%).

Workup

extractionextracted with tetrahydrofuran/ethyl acetate
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record: ord-ae8ee79fdad846a3a154664c5fdd02bc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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