Benzenamine, 4-fluoro-N-(1-methylethyl)- → N-(4-fluorophenyl)-N-isopropyl-2-(2-propynyl)-N'-((E)-styrylsulfonyl)malonamide

HRID 1256919Notes

Reaction equation

HRID 1256919 reaction equation
C(N(CC)[C:4](=[O:25])[CH:5]([CH2:22][C:23]#[CH:24])[C:6]([NH:8][S:9]([C:12]1C=C[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])=[O:7])C.C(/S(N)(=O)=O)=C\C1C=CC=CC=1.[F:40][C:41]1[CH:50]=[CH:49][C:44]([NH:45][CH:46]([CH3:48])[CH3:47])=[CH:43][CH:42]=1>>[F:40][C:41]1[CH:50]=[CH:49][C:44]([N:45]([CH:46]([CH3:48])[CH3:47])[C:4](=[O:25])[CH:5]([CH2:22][C:23]#[CH:24])[C:6]([NH:8][S:9](/[CH:12]=[CH:13]/[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:10])=[O:7])=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-HCID 5357731(1E)-2-PhenylethenesulfonamideHCID 86645224N,N-diethyl-N'-(2-naphthylsulfonyl)-2-(2-propynyl)malonamide

Product 1

HCID 86645227N-(4-fluorophenyl)-N-isopropyl-2-(2-propynyl)-N'-((E)-styrylsulfonyl)malonamideYield 36.4%

Procedure

In the same manner as in Example 152 (3), the object compound was obtained using the compound (3.00 g) obtained in Example 152 (2) and trans-β-styrenesulfonamide (3.23 g). This was subjected to hydrolysis in the same manner as in Example 1 (3), and condensed with 4-fluoro-N-isopropylaniline (1.29 g) in the same manner as in Example 1 (4) to give a crude product. This was purified by silica gel column chromatography to give the title compound (1.25 g) as a white powder.

Workup

  1. customto give a crude product
  2. customThis was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-64b9239aa5774de7b9aa6448f11cb14e
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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