Triethylamine → methyl 4-chloro-1-(3-chloropropyl)-2-[(2-methoxy-4,6-dimethylpyrimidin-5-yl)amino]1H-benzimidazole-7-carboxylate

HRID 1628603Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][Cl:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[N:18]([C:21]1[C:22]([CH3:30])=[N:23][C:24]([O:28][CH3:29])=[N:25][C:26]=1[CH3:27])=[C:19]=S.C(=O)([O-])O.[Na+].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.O>[Cl:12][C:11]1[C:2]2[N:1]=[C:19]([NH:18][C:21]3[C:26]([CH3:27])=[N:25][C:24]([O:28][CH3:29])=[N:23][C:22]=3[CH3:30])[N:13]([CH2:14][CH2:15][CH2:16][Cl:17])[C:3]=2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-chloropropyl)amino]benzoate (500 mg, 1.80 mmol), 5-isothiocyanato-2-methoxy-4,6-dimethylpyrimidine (527 mg, 2.70 mmol) and sodium hydrogen carbonate (454 mg, 5.40 mmol) in tetrahydrofuran (1 mL) was stirred at 60° C. for 36 h. After tetrahydrofuran (4 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (345 mg, 1.80 mmol) and triethylamine (0.251 mL, 1.80 mmol) were added to the mixture at room temperature, the resultant mixture was stirred at 50° C. for 40 min and poured into water (50 mL). The precipitate was collected by filtration and washed with water and diethyl ether to afford the title compound as a colorless solid (589 mg, 1.34 mmol, 74%).

Workup

filtrationThe precipitate was collected by filtration
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-97a9729eed284b23881f72537a1fdaaf
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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