4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → 4-(2-(3-(3-Cyanophenyl)-1-methylureido)ethyl)phenylboronic acid

HRID 735556Notes

Reaction equation

HRID 735556 reaction equation
C(C1C=C(NC(=O)C[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]([OH:27])[OH:26])=[CH:21][CH:20]=2)C=CC=1S(CC)(=O)=O)#N.BrC1C=CC(C[CH2:35][N:36](C)[C:37]([NH:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]#[N:47])[CH:41]=2)=[O:38])=CC=1>>[C:46]([C:42]1[CH:41]=[C:40]([NH:39][C:37](=[O:38])[N:36]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([B:25]([OH:26])[OH:27])=[CH:23][CH:24]=2)[CH3:35])[CH:45]=[CH:44][CH:43]=1)#[N:47]

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 578428191-(4-Bromophenethyl)-3-(3-cyanophenyl)-1-methylurea

Product 1

HCID 578426104-(2-(3-(3-Cyanophenyl)-1-methylureido)ethyl)phenylboronic acidYield 91%

Procedure

Using a procedure analogous to that used to prepare 6D, 23C (200 mg, 0.70 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 23D (165 mg, 91%) as a yellow oil. MS (ESI) m/z 324.03 (M+H)+.

Sources & evidence

ORD record
ord-6f563273d4994cbb87e004ccaa213958
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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