4-Acetylphenylboronic acid → HCID 86594580, compound

HRID 1744146Notes

Reaction equation

HRID 1744146 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:29])[C@H:6]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16](N3CCNCC3)=[CH:15][CH:14]=2)=[CH:11][S:10][N:9]=1)#[N:2].[C:30](C1C=CC(B(O)O)=CC=1)(=[O:32])[CH3:31]>>[C:30]([C:16]1[CH:15]=[CH:14][C:13]([C:12]2[C:8]([NH:7][C@H:6]([C:5]([NH:4][CH2:3][C:1]#[N:2])=[O:29])[CH2:25][CH:26]([CH3:27])[CH3:28])=[N:9][S:10][CH:11]=2)=[CH:18][CH:17]=1)(=[O:32])[CH3:31]

Participants

3

Reactant 2

HCID 37021224-Acetylphenylboronic acidHCID 86594560HCID 86594560, compound

Product 1

HCID 86594580HCID 86594580, compound

Procedure

N2-(4-bromoisothiazol-3-yl)-N1-(cyanomethyl)leucinamide (100 mg, 0.30 mmol, prepared as described in Example 13) was submitted to a Suzuki coupling with 4-acetylphenylboronic acid (99 mg, 0.60 mmoles) as described in Example 1 to afford N2-[4-(4-acetylphenyl)isothiazol-3-yl]-N1-(cyanomethyl)leucinamide which was purified by flash chromatography (30% to 55% EtOAc/hexanes).

Sources & evidence

ORD record
ord-73926c9f88a440ea84e8d23a0a2656c2
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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