3-Nitro-1-(2,4,6-trimethylbenzene-1-sulfonyl)-1H-1,2,4-triazole → {(5-Chloro-benzo[b]thiophen-3-yl)-[2-(3,4-difluoro-phenyl)-vinylcarbamoyl]-methyl}-methyl-phosphinic acid diethylcarbamoylmethyl ester

HRID 1034930Notes

Reaction equation

HRID 1034930 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[S:6][CH:7]=[C:8]([CH:9]([P:23]([CH3:26])(=[O:25])[OH:24])[C:10](=[O:22])[NH:11][CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=3)[C:4]=2[CH:3]=1.[CH2:29]([N:31]([CH2:36][CH3:37])[C:32](=[O:35])[CH2:33]O)[CH3:30].CC1C=C(C)C(S(N2N=C([N+]([O-])=O)N=C2)(=O)=O)=C(C)C=1>N1C=CC=CC=1>[CH2:29]([N:31]([CH2:36][CH3:37])[C:32]([CH2:33][O:25][P:23]([CH:9]([C:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:28]=[CH:27][C:5]=2[S:6][CH:7]=1)[C:10](=[O:22])[NH:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)([CH3:26])=[O:24])=[O:35])[CH3:30]

Participants

5

Reactant 3

HCID 7169013-Nitro-1-(2,4,6-trimethylbenzene-1-sulfonyl)-1H-1,2,4-triazoleHCID 4137580N,N-Diethyl-2-hydroxyacetamideHCID 66871866[(5-Chloro-benzo[b]thiophen-3-yl)-[2-(3,4-difluoro-phenyl)-vinylcarbamoyl]-methyl}-methyl-phosphinic acid

Product 1

HCID 66678309{(5-Chloro-benzo[b]thiophen-3-yl)-[2-(3,4-difluoro-phenyl)-vinylcarbamoyl]-methyl}-methyl-phosphinic acid diethylcarbamoylmethyl esterYield 44.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the procedure described in Example 47, Compound 17 (0.25 g, 0.57 mmol), N,N-diethyl-2-hydroxyacetamide (0.37 g, 2.86 mmol), and MSNT (0.25 g, 0.86 mmol) in pyridine (5 ml) yielded 0.14 g of Compound 185, as a white powder (−3:1 mixture of diastereomers). HPLC: 4.03 min (24%), 4.11 min (76%); MS (ES) m/z 555 (MH+).

Sources & evidence

ORD record
ord-78bdd79734874c85b5e219b58d4634c0
Source dataset
uspto-grants-2013_10
Patent number
US08546358B2

Reaction notes

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