4-Fluoro-2-methylbenzonitrile → HCID 66818775, compound

HRID 1024762Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([CH3:43])[CH:36]=1>>[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:32])[C:16]2[CH:17]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:19]=[C:20]([O:22][C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([CH3:43])[CH:36]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 38260554-Fluoro-2-methylbenzonitrile

HCID 66818660HCID 66818660, compound

Product 1

HCID 66818775HCID 66818775, compoundYield 71.3%

Procedure

Following the procedure of Example 69(b) {4-[3-(4-cyanophenoxy)-5-hydroxy-benzoylamino]cyclohexyl}carbamic acid tert-butyl ester 0.85 g (1.88 mmol) and 4-fluoro-2-methyl-benzonitrile (0.508 g, 3.76 mmol) were used to afford 0.76 g of the required product. 1H NMR (DMSO-d6): δ 1.20 (4H, m), 1.4 (9H, s), 1.8 (4H, m), 2.45 (3H, s), 3.15 (1H, m), 3.7 (1H, m), 6.72 (1H, d), 7.02 (1H, d), 7.2 (4H, m), 7.5 (2H, s), 7.8 (1H, d), 7.88 (2H, d), 8.34 (1H, d).

Sources & evidence

ORD record: ord-28c7c1f8eb5e405d8d6beff0bddab585
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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