Tetrahydrofuran → 4-[5-Bromo-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 723116Notes

Reaction equation

HRID 723116 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16](Cl)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[NH2:23][CH2:24][C:25]1[CH:26]=[N:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=1.C(N(C(C)C)CC)(C)C.C1COCC1>CCOC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([NH:23][CH2:24][C:25]3[CH:26]=[N:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=3)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 210571794-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 695865644-[5-Bromo-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The reaction was conducted following the procedure for Example 156: step a, using 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.050 g, 0.113 mmol), (Example 2: step c), 3-aminomethyl-6-trifluoromethyl pyridine (0.026 g, 0.146 mmol), diisopropylethylamine (0.073 g, 0.565 mmol), THF [0.5 mL], DMF [0.5 mL]. Chromatography of the residue (25%–50% EtOAc/Hx) yielded the title compound. ESI-MS (m/z): Calcd. For C19H15BrN3O4S3: 583.44 (M+H); found 582.0, 583.9.

Sources & evidence

ORD record
ord-ee220cadabad438bb23e8b0235902a56
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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