Tetrahydrofuran → 1-{4'-[4-(2-Benzyl-cyclohexylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1183260Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH2:27])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:28]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][C:36]1=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1COCC1.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][CH:36]4[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]4[CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.200 g, 0.55 mmol) and 2-benzylcyclohexanone (0.156 g, 0.83 mmol) were combined in toluene and stirred at 110° C. for 1 hour. After cooling to room temperature, THF was added, followed by sodium cyanoborohydride (0.086 g, 1.37 mmol), and the reaction was stirred at room temperature for 2 hours. The mixture was adsorbed onto silica gel and purified by silica gel chromatography to give the title compound.

Workup

temperatureAfter cooling to room temperature
stirringthe reaction was stirred at room temperature for 2 hours
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-51138e95e9f94a4fbb24dbba1eaf37b4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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