4-Fluorobenzonitrile → HCID 66818468, compound

HRID 1024793Notes

Reaction equation

[C:1]([O:5][C:6](=[O:41])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:40])[C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:27][CH:26]=3)[CH:18]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].F[C:43]1[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=1>>[C:1]([O:5][C:6](=[O:41])[NH:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:40])[C:17]2[CH:22]=[C:21]([O:23][C:43]3[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=3)[CH:20]=[C:19]([O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:27][CH:26]=3)[CH:18]=2)[CH2:14][CH2:15]1)([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 145174-Fluorobenzonitrile

HCID 66818688HCID 66818688, compound

Product 1

HCID 66818468HCID 66818468, compoundYield 43.3%

Procedure

Using 1.2 g (2.1 mmol) of [2-(1-{3-[4-(tert-Butoxycarbonylamino-methyl)-phenoxy]-5-hydroxy-benzoyl}-piperidin-4-yl)-ethyl]carbamic acid tert-butyl ester and 4-fluorobenzonitrile (0.5 g, 4.2 mmol) and following the procedure of Example 42(b) afforded 0.610 g of the required product. Percentage purity (LCMS): 89.1%, (M+1)=670.3+1.

Sources & evidence

ORD record: ord-45f5173d6fa844feb3a9b51808b27f3c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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