4-Fluoro-3-(trifluoromethyl)benzonitrile → HCID 66818703, compound

HRID 1024779Notes

Reaction equation

[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:39])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][C:43]=1[C:50]([F:53])([F:52])[F:51]>>[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:39])[C:16]2[CH:21]=[C:20]([O:22][C:42]3[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][C:43]=3[C:50]([F:51])([F:52])[F:53])[CH:19]=[C:18]([O:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:29]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

HCID 66818915HCID 66818915, compound

Product 1

HCID 66818703HCID 66818703, compoundYield 50.5%

Procedure

Using 0.46 g (0.82 mmol) of {4-[3-[4-tert-butoxycarbonylaminomethylphenoxy]-5-hydroxybenzoylamino]-cyclohexyl}carbamic acid tert-butyl ester and 4-fluoro-3-tri-fluoromethylbenzonitrile (0.313 g, 1.65 mmol) and following the procedure of Example 42(b) afforded 0.3 g of the required product. NMR (DMSO-d6): δ 1.25 (4H, m), 1.38 (18H, d), 1.8 (4H, m), 3.18 (1H, m), 3.64 (1H, m), 4.12 (2H, d), 6.75 (1H, d), 7.02 (1H, s), 7.08 (2H, d), 7.20 (1H, d), 7.28 (2H, d), 7.41 (3H, m), 8.1 (1H, m), 8.38 (2H, m).

Sources & evidence

ORD record: ord-68f4f08f03514866a546bcc7aa31871c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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