4-(Bromomethyl)benzonitrile → HCID 70975625, compound

HRID 1190803Notes

Reaction equation

HRID 1190803 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([N:11]3[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18](=[O:20])[OH:19])[CH2:12]3)=[C:5]2[NH:4][C:3]1=[O:21].Br[CH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1>>[C:24]([O:20][C:18](=[O:19])[NH:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]3[N:2]([CH3:1])[C:3](=[O:21])[N:4]([CH2:23][C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[C:5]=23)[CH2:12]1)([CH3:31])([CH3:25])[CH3:23]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 86673549HCID 86673549, compound

Product 1

HCID 70975625HCID 70975625, compoundYield 126.1%

Procedure

The specific operation referred to the step (5) described in Example 1 for details. 347 mg (R)-1-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl)piperidin-3-yl carbamic acid ter.-butyl ester (1 mmol) and 235 mg 4-(bromomethyl)benzonitrile (1.2 mmol) were charged. A column chromatography was performed to afford 350 mg titled product with a yield of 75.6%.

Sources & evidence

ORD record
ord-4d534924229446f0941739f8149e2a83
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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