4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → HCID 57842869, compound

HRID 735607Notes

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:53])[O:39][CH2:40][CH2:41][C:42]2[C:47]([CH2:48][CH3:49])=[CH:46][C:45](Br)=[CH:44][C:43]=2[CH2:51][CH3:52])[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[C:47]([CH2:48][CH3:49])=[CH:46][C:45]([B:25]([OH:27])[OH:26])=[CH:44][C:43]=2[CH2:51][CH3:52])=[O:53])[CH:34]=[CH:35][CH:36]=1)#[N:30]

Participants

Reactant 2

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

HCID 57842786HCID 57842786, compound

Product 1

HCID 57842869HCID 57842869, compoundYield 45%

Procedure

Using a procedure analogous to that used to prepare 6D, 37D (670 mg, 1.7 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 37E (278 mg, 45%) as a brown oil. 1H NMR (400 MHz, CD3OD) δ ppm 1.16 (t, J=7.45 Hz, 6 H) 2.68 (q, J=7.41 Hz, 4 H) 3.03 (t, J=7.83 Hz, 2 H) 4.14 (t, J=7.82 Hz, 2 H) 7.13-7.29 (m, 2 H) 7.30-7.45 (m, 2 H) 7.59 (d, J=7.83 Hz, 1 H) 7.80 (s, 1 H) 9.42 (s, 1 H).

Sources & evidence

ORD record: ord-0badc83b1c7a4e8a9cf56cf1881f453f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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