1-(3-(4-Bromophenyl)propyl)-3-(3-cyanophenyl)-1-methylurea → 4-(3-(3-(3-Cyanophenyl)-1-methylureido)propyl)phenylboronic acid

HRID 735551Notes

Reaction equation

HRID 735551 reaction equation
C(C1C=C(NC(=O)[CH2:16][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(CC[CH2:38][N:39](C)[C:40]([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]#[N:50])[CH:44]=2)=[O:41])=CC=1>>[C:49]([C:45]1[CH:44]=[C:43]([NH:42][C:40](=[O:41])[N:39]([CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([B:25]([OH:26])[OH:27])=[CH:23][CH:24]=2)[CH3:38])[CH:48]=[CH:47][CH:46]=1)#[N:50]

Participants

3

Reactant 2

HCID 578426211-(3-(4-Bromophenyl)propyl)-3-(3-cyanophenyl)-1-methylureaHCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

Product 1

HCID 578427124-(3-(3-(3-Cyanophenyl)-1-methylureido)propyl)phenylboronic acidYield 91%

Procedure

Using a procedure analogous to that used to prepare 6D, 22C (210 mg, 0.54 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 22D (146 mg, 91%) as a clear oil. MS (ESI) m/z 338.3 (M+H)+.

Sources & evidence

ORD record
ord-c95e90e2e3b64162818a7c9c3ad2dc26
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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