HCID 10112187, compound → HCID 10203688, compound

HRID 2417278Notes

Reaction equation

C([O:5]C1C=CC(SC(C2C=CC(C3SC=CC=3)=CC=2)C(NO)=O)=CC=1)C#CC.[CH2:29]([O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH:42]([C:47]2[CH:52]=[CH:51][C:50]([C:53]3[S:54][CH:55]=[CH:56][CH:57]=3)=[CH:49][CH:48]=2)[C:43]([NH:45][OH:46])=[O:44])=[O:41])=[CH:36][CH:35]=1)[C:30]#[C:31][CH3:32]>>[CH2:29]([O:33][C:34]1[CH:35]=[CH:36][C:37]([S:40]([CH:42]([C:47]2[CH:52]=[CH:51][C:50]([C:53]3[S:54][CH:55]=[CH:56][CH:57]=3)=[CH:49][CH:48]=2)[C:43]([NH:45][OH:46])=[O:44])(=[O:5])=[O:41])=[CH:38][CH:39]=1)[C:30]#[C:31][CH3:32]

Participants

Reactant 2

HCID 10112187HCID 10112187, compound

HCID 22634064HCID 22634064, compound

Product 1

HCID 10203688HCID 10203688, compoundYield 26%

Procedure

Starting from a mixture of 2{[4-(2-butynyloxy)phenyl]sulfanyl}-N-hydroxy-2-[4-(2-thienyl)phenyl]acetamide and 2-{[4-(2-butynyloxy)phenyl]sulfinyl}-N-hydroxy-2-[4-(2-thienyl)phenyl]ethanamide (410 mg, 0.96 mmol), and following the procedure as outlined in Example 75, 110 mg of 2-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-2-[4-(2-thienyl)phenyl]acetamide was isolated as a gray solid. mp: 175° C.; Yield: 26%; MS: 442.2 (M+W)+; 1H NMR (300 MHz, DMSO-d6): δ 1.83 (t, 3H), 4.85 (d, J=2.01 Hz, 2H), 5.04 (s, 1H), 7.11 (m, 4H), 7.39 (d, 7.49-7.63 (band, 5H), 9.30 (s, 1H), 10.9 (s, 1H).

Sources & evidence

ORD record: ord-13414f2bbd1c42fda4a782679a5bf678
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825354B2

Reaction notes

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