4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → HCID 68818426, compound

HRID 735564Notes

Reaction equation

C(C1C=C(NC(=O)CCCC2C=CC([B:25]([OH:27])[OH:26])=CC=2)C=CC=1S(CC)(=O)=O)#N.[C:29]([C:31]1[CH:32]=[C:33]([NH:42][C:43](=[O:54])[O:44][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50](Br)=[CH:49][CH:48]=2)[CH:34]=[CH:35][C:36]=1[S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])#[N:30]>>[C:29]([C:31]1[CH:32]=[C:33]([NH:42][C:43]([O:44][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([B:25]([OH:27])[OH:26])=[CH:49][CH:48]=2)=[O:54])[CH:34]=[CH:35][C:36]=1[S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])#[N:30]

Participants

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid

HCID 68819124HCID 68819124, compound

Product 1

HCID 68818426HCID 68818426, compoundYield 82%

Procedure

Using a procedure analogous to that used to prepare 6D, 26A (600 mg, 2.54 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 26B (455 mg, 82%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.24 (t, J=7.47 Hz, 3 H) 3.01 (t, J=6.81 Hz, 2 H) 3.35 (q, J=7.32 Hz, 2 H) 4.42 (t, J=6.59 Hz, 2 H) 7.29 (d, J=7.91 Hz, 2 H) 7.56 (d, J=7.91 Hz, 2 H) 7.86 (dd, J=9.01, 1.98 Hz, 1 H) 7.99 (d, J=8.79 Hz, 1 H) 8.11 (d, J=2.20 Hz, 1 H) 10.12 (s, 1 H).

Sources & evidence

ORD record: ord-d0a8ad53a19548d0a5892af865aaf269
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

Loading…