4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → HCID 57842579, compound

HRID 735578Notes

Reaction equation

HRID 735578 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:37][C:38](=[O:50])[O:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45](Br)=[CH:44][C:43]=2[CH3:49])[CH:34]=[CH:35][CH:36]=1)#[N:30]>>[C:29]([C:31]1[CH:32]=[C:33]([NH:37][C:38]([O:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([B:25]([OH:27])[OH:26])=[CH:44][C:43]=2[CH3:49])=[O:50])[CH:34]=[CH:35][CH:36]=1)#[N:30]

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 578428474-Bromo-2-methylphenethyl 3-cyanophenylcarbamate

Product 1

HCID 57842579HCID 57842579, compoundYield 64%

Procedure

Using a procedure analogous to that used to prepare 6D, 30C (730 mg, 2.0 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 30D (420 mg, 64%) as a brown oil. 1H NMR (400 MHz, MeOD) δ ppm 2.29 (s, 3 H) 2.94 (t, J=7.07 Hz, 2 H) 4.26 (t, J=7.07 Hz, 2 H) 7.11 (d, J=7.33 Hz, 1 H) 7.24 (d, J=7.58 Hz, 1 H) 7.33 (t, J=7.96 Hz, 1 H) 7.36-7.52 (m, 2 H) 7.56 (d, J=7.83 Hz, 1 H) 7.77 (s, 1 H).

Sources & evidence

ORD record
ord-660d480eeed94f84b951b67d79b3d839
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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