HCID 21937555, compound → HCID 73690429, compound

HRID 2121981Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][CH3:17])=[C:11]([N+:18]([O-])=O)[CH:10]=1)=[O:7])(=[O:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:32]([N:39]1[C:43](=[O:44])[C:42](=[C:45]2[N:49]([CH3:50])[C:48]3[CH:51]=[CH:52][CH:53]=[CH:54][C:47]=3[S:46]2)[S:41][CH2+:40]1SC)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([N:39]1[C:43](=[O:44])[C:42](=[C:45]2[N:49]([CH3:50])[C:48]3[CH:51]=[CH:52][CH:53]=[CH:54][C:47]=3[S:46]2)[S:41][C:40]1=[N:18][C:11]1[CH:10]=[C:9]([NH:8][C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:7])[CH:14]=[CH:13][C:12]=1[NH:15][CH2:16][CH3:17])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Reactant 1

HCID 21937555HCID 21937555, compound

Product 1

HCID 73690429HCID 73690429, compound

Procedure

In a manner similar to Example 30, intermediate 2-acetoxy-4′-ethylamino-3′-nitroacetanilide was hydrogenated and then condensed with 3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate to afford the title compound. 1H-NMR (CDCl3): δ 7.73 (1H, br s), 7.44-7.51 (3H, m), 7.23-7.34 (5H, m), 7.16 (1H, t), 7.08 (1H, dd), 7.00 (1H, d), 6.56 (1H, d), 5.15 (2H, s), 4.67 (2H, s), 3.74 (3H, s), 2.98 (2H, q), 2.20 (3H, s), 1.00 (3H, t); MS(ESI): 588 (MH+).

Sources & evidence

ORD record: ord-e71154e8244749439577939fda0bc42f
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696473B2

Reaction notes

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