4-(Bromomethyl)benzonitrile → HCID 66818892, compound

HRID 1024766Notes

Reaction equation

HRID 1024766 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=2[OH:23])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1>>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=3)=[CH:18][C:17]=2[O:23][CH2:27][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 66818491HCID 66818491, compound

Product 1

HCID 66818892HCID 66818892, compoundYield 76.3%

Procedure

[4-(2,4-Dihydroxy benzoylamino)cyclohexyl]carbamic acid tert-butyl ester (0.95 g, 2.71 mmol) and 4-bromomethyl-benzonitrile (2.12 g, 10.84 mmol) and other reagents as described in Example 75(a) were used to afford 1.2 g of the required product. 1H NMR (DMSO-d6): δ 1.20 (5H, m), 1.4 (9H, m), 1.75 (4H, m), 3.6 (1H, m), 5.3 (4H, s), 6.7 (1H, s), 6.85 (1H, s), 7.35 (2H, d), 7.5 (1H, s), 7.75 (4H, d), 7.9 (4H, s).

Sources & evidence

ORD record
ord-35c3266a90054034a84be926d21376e6
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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