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

HRID 2216055Notes

Reaction equation

HRID 2216055 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([C:10]1[S:11][C:12]([S:33][CH3:34])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([Cl:31])=[CH:26][C:25]=3[NH2:32])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:43][S:44]([CH2:47][CH2:48][CH2:49][C:50](Cl)=[O:51])(=[O:46])=[O:45]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]([C:10]1[S:11][C:12]([S:33][CH3:34])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([Cl:31])=[CH:26][C:25]=3[NH:32][C:50](=[O:51])[CH2:49][CH2:48][CH2:47][S:44]([CH3:43])(=[O:46])=[O:45])[CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218866174-Methanesulfonyl-butyryl chlorideHCID 145857635tert-butyl N-[4-[3-(2-amino-4-chloro-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857681tert-butyl N-[4-[3-[4-chloro-2-methyl-6-(4-methylsulfonylbutanoylamino)phenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{[4-(2′-Amino-4′-chloro-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (120 mg, 0.22 mmol, Example 135, e) and Et3N (0.91 μL, 0.65 mmol) were dissolved into DCM (4 mL). To this was added (4-Methanesulfonyl-butyryl chloride (0.144 M, 3.1 mL, 0.44 mmol, Example 209: a) and the reaction was stirred at RT overnight. The solvents were removed in vacuo followed by purification by flash column chromatography (20% EtOAc/hexanes) that yielded the title compound as an orange solid (124 mg, 81%). ESI-MS (m/z): Calcd. for C29H34ClN3O7S4: 700.1 (M+1) found: 700.1.

Workup

  1. customThe solvents were removed in vacuo
  2. customfollowed by purification by flash column chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c24919e929f54e7b814612b14b09ea56
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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