3-Cyanobenzoic acid → HCID 22716894, compound

HRID 1352841Notes

Reaction equation

HRID 1352841 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[N:2].[C:12](C1NC=CN=1)([C:14]1[NH:15]C=CN=1)=[O:13].[CH:24]1[CH:29]=[CH:28][C:27]([C@@H](N)CO)=[CH:26][CH:25]=1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:15]([C:27]1[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=1)[CH2:14][CH2:12][OH:13])=[O:8])#[N:2]

Participants

4

Reactant 3

HCID 158753-Cyanobenzoic acidHCID 2724025(R)-beta-aminophenethyl alcoholHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 22716894HCID 22716894, compound

Procedure

By solution phase srategy: Typically 3-cyanobenzoic acid is activated with carbonyl-diimidazole and reacted with R-phenylglycinol to give 3-cyanobenzoylphenylglycinol. Reaction with a trichloroacetimidate and BF3 etherate, (4), gives an ether. Reaction of the cyano group with HCl in ethanol followed by ammonia in ethanol gives the amidino compound.

Sources & evidence

ORD record
ord-b1f4ae3ef5cf4c6c86426d260a8df36c
Source dataset
uspto-grants-2007_05
Patent number
US07220781B2

Reaction notes

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