Benzonitrile, 3-(bromomethyl)- → HCID 66818795, compound

HRID 1024769Notes

Reaction equation

HRID 1024769 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:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[C:31]#[N:32]>>[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][CH:33]=[C:30]([C:31]#[N:32])[CH:29]=3)=[CH:18][C:17]=2[O:23][CH2:27][C:28]2[CH:35]=[CH:34][CH:33]=[C:30]([C:31]#[N:32])[CH:29]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 66818491HCID 66818491, compound

Product 1

HCID 66818795HCID 66818795, compoundYield 53.4%

Procedure

[4-(2,4-Dihydroxy benzoylamino)cyclohexyl]carbamic acid tert-butyl ester (0.85 g, 2.42 mmol) and 3-bromomethyl-benzonitrile (1.89 g, 9.68 mmol) and other reagents as described in Example 75(a) were used to afford 0.75 g of the required product. 1H NMR (DMSO-d6): δ 1.4 (9H, s), 1.75 (4H, m), 3.15 (1H, m), 3.65 (2H, m), 4.55 (1H, m), 5.25 (4H, s), 6.72 (2H, m), 6.9 (1H, s), 7.7 (6H, m), 7.85 (4H, m), 7.94 (1H, s), 8.04 (1H, s).

Sources & evidence

ORD record
ord-97965c56ed4d4ed58404d3b2999d5dbb
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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