4-Fluorobenzonitrile → HCID 66818418, compound

HRID 1024774Notes

Reaction equation

[C:1]([O:5][C:6](=[O:38])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:37])[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][CH2:35][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:40]1[CH:47]=[CH:46][C:43]([C:44]#[N:45])=[CH:42][CH:41]=1>>[C:1]([O:5][C:6](=[O:38])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:37])[C:16]2[CH:17]=[C:18]([O:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][NH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][CH:29]=3)[CH:19]=[C:20]([O:22][C:40]3[CH:47]=[CH:46][C:43]([C:44]#[N:45])=[CH:42][CH:41]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:2])([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 145174-Fluorobenzonitrile

HCID 66818628HCID 66818628, compound

Product 1

HCID 66818418HCID 66818418, compoundYield 91.5%

Procedure

Using 0.56 g (1.06 mmol) of (4-{3-[4-(Ethoxycarbonylamino-methyl)-phenoxy]-5-hydroxy-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl ester and 4-fluoro-benzonitrile (0.32 g, 2.65 mmol) and following the procedure of Example 42(b) afforded 0.61 g of the required product. Percentage purity (LCMS): 45.2%, (M+1)=628.3+1.

Sources & evidence

ORD record: ord-bf125cab9c434fe79dddd979590b706f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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