Furfurylamine → 4-[1-(4-Cyano-3-trifluoromethyl-phenoxymethyl)-2,2-dimethyl-cyclopropoxy]-2-trifluoromethyl-benzonitrile

HRID 1452611Notes

Reaction equation

[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[N:2].[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=N[C:26]=2[CH:27]=1.O1C=CC=C1[CH2:37][NH2:38].N=C=N>CN(C=O)C>[C:37]([C:25]1[CH:24]=[CH:23][C:22]([O:11][CH2:9][C:8]2([O:7][C:6]3[CH:16]=[CH:17][C:3]([C:1]#[N:2])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=3)[CH2:12][C:13]2([CH3:15])[CH3:14])=[CH:27][C:26]=1[C:18]([F:21])([F:20])[F:19])#[N:38]

Participants

Conditions

Temperature: 70 °C

Procedure

To 1 mL of 0.1M(molar) solutions of the 2-(4-Cyano-3-trifluoromethyl-phenoxy)-4-methyl-pentanoic acid in DMF(dimethylformamide) (0.1 mmol) were added 0.5 mL of a 0.376M solution of HOBT, 1-hydroxybenztriaole, (0.2 mmol) in DMF, 0.1 mL of a 0.1M solution of the C-furan-2-yl-methylamine (0.1 mmol) in DMF, and approximately 183 mg of silica bound carbodiimide (loading: 1.09 g/mmol, 0.2 mmol). The resultant mixtures were shaken and heated at 70° C. for approximately 18 h. The reactions were filtered and the resin thoroughly rinsed with DMF. The solvent was removed in-vacuo to obtain oils that were then purified by HPLC(high performance liquid chromatography).

Workup

filtrationThe reactions were filtered
washthe resin thoroughly rinsed with DMF
customThe solvent was removed in-vacuo
customto obtain oils that
customwere then purified by HPLC(high performance liquid chromatography)

Sources & evidence

ORD record: ord-e72024fd52bb4220b3db60fc39bcd234
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473711B2

Reaction notes

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