Dimethylformamide → cis-N-[1-[3-(4-Fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

HRID 935

Reaction equation

[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C:10](=[O:25])[C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=2[O:19][C@@H:20]([CH3:24])[C:21]#[C:22][CH3:23])[CH2:7][CH2:6][NH:5][CH2:4]1.[F:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34]Br)=[CH:29][CH:28]=1.C(N(CC)CC)C.CN(C=O)C>C(OCC)(=O)C>[F:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH2:33][CH2:34][N:5]2[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:25])[C:11]3[CH:16]=[C:15]([Cl:17])[C:14]([NH2:18])=[CH:13][C:12]=3[O:19][C@@H:20]([CH3:24])[C:21]#[C:22][CH3:23])[C@H:3]([O:2][CH3:1])[CH2:4]2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtained mixture was washed with water thrice, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane) to give 0.13 g of the title compound.

Workup

temperaturecooled
washThe obtained mixture was washed with water thrice
dry with materialdried over magnesium sulfate
customThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-e90e3b33efd8427982a8d67e8d113a2f
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723472

Linked notes

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