4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → HCID 68818193, compound

HRID 735643Notes

Reaction equation

HRID 735643 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:51])[O:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45](Br)=[CH:44][C:43]=2[CH2:49][CH3:50])[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[CH2:49][CH3:50])=[O:51])[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 68817589HCID 68817589, compound

Product 1

HCID 68818193HCID 68818193, compoundYield 61%

Procedure

Using a procedure analogous to that used to prepare 6D, 56A (630 mg, 1.69 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 56B (350 mg, 61%) as a solid. 1H NMR (400 MHz, MeOD-d4) δ ppm 0.98 (t, 3 H) 2.42 (q, 2 H) 2.73 (t, 2 H) 4.10 (t, 2 H) 6.82 (d, 1 H) 7.02 (d, 1 H) 7.09 (t, 2 H) 7.15 (t, 1 H) 7.36 (d, 1 H) 7.58-7.63 (m, 1 H).

Sources & evidence

ORD record
ord-170e098e906a4f4290afbc825af314c9
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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