Triethylamine → tert-butyl N-[4-[3-[2-methyl-6-(4-methylsulfonylbutanoylamino)phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723172Notes

Reaction equation

HRID 723172 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][C:8](Cl)=[O:9])(=[O:4])=[O:3].[C:11]([O:15][C:16](=[O:44])[NH:17][C:18]([C:20]1[S:21][C:22]([S:42][CH3:43])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH2:41])[CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:24]=1)=[NH:19])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:44])[NH:17][C:18](=[NH:19])[C:20]1[S:21][C:22]([S:42][CH3:43])=[C:23]([S:25]([C:28]2[CH:29]=[C:30]([C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[NH:41][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:31]=[CH:32][CH:33]=2)(=[O:26])=[O:27])[CH:24]=1)([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218866174-Methanesulfonyl-butyryl chlorideHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857696tert-butyl N-[4-[3-[2-methyl-6-(4-methylsulfonylbutanoylamino)phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methanesulfonyl-butyryl chloride (0.333 g, 1.81 mmol) [example 209, step a] was added to a solution of {[4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.468 g, 0.905 mmol) [example 25, step c] and triethylamine (1.83 g, 18.1 mmol) in dichloromethane at room temperature. The reaction was stirred for 24 hours and then evaporated. Column chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (0.520 g, 78%) as a solid. ESI-MS (m/z): Calcd. for C29H35N3O7S4: 665.14; found: 665.8.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-9224f23ad50b4f22be9fb2847d751692
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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