Pyridine → N-[4-Chloro-3-cyclopropylaminocarbonyl-phenyl]-2-chloro-5-(5-chloro-thien-2-yl)carbonylaminomethyl-benzamide

HRID 1846098Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8].N1C=CC=CC=1.[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([C:35]2[S:36][C:37]([Cl:40])=[CH:38][CH:39]=2)=[O:34])=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C(#N)C.O>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[C:28]([CH2:31][NH:32][C:33]([C:35]3[S:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[O:34])[CH:29]=[CH:30][C:22]=2[Cl:21])=[CH:13][C:6]=1[C:7]([NH:9][CH:10]1[CH2:11][CH2:12]1)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To 2.0 mL of a 0.05 M solution of 5-amino-2-chloro-N-cyclopropyl-benzamide (0.10 mmol) in acetonitrile was added pyridine (20 μL, 0.25 mmol) and then 1.0 mL of a 0.05 M solution of 2-chloro-5-(5-chloro-thien-2-yl)carbonylaminomethyl-benzoyl chloride (0.10 mmol, prepared from 5-(aminomethyl)-2-chloro-benzoic acid in analogy to step 1c and 1d) in acetonitrile. The reaction mixture was stirred overnight at 60° C., diluted with 200 μL of distilled water and filtered over Alox B. The Alox B pad was washed three times with 2.0 mL 9:1 DMF/MeOH-solution and the combined filtrate was concentrated in vacuo. The residue was dissolved in 2.0 mL of DMF and purified via prep. HPLC.

Workup

filtrationfiltered over Alox B
washThe Alox B pad was washed three times with 2.0 mL 9:1 DMF/MeOH-solution
concentrationthe combined filtrate was concentrated in vacuo
dissolutionThe residue was dissolved in 2.0 mL of DMF
custompurified via prep

Sources & evidence

ORD record: ord-1cce408dd085412e860a90ac83551cb1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951999B2

Reaction notes

Loading…