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

HRID 723133Notes

Reaction equation

HRID 723133 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[NH2:31])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:42][S:43]([CH2:46][CH2:47][CH2:48][C:49](Cl)=[O:50])(=[O:45])=[O:44]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8](=[NH:9])[C:10]1[S:11][C:12]([S:32][CH3:33])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:25]([NH:31][C:49](=[O:50])[CH2:48][CH2:47][CH2:46][S:43]([CH3:42])(=[O:45])=[O:44])=[CH:26][CH:27]=[CH:28][C:29]=3[CH3:30])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

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 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{[4-(6′-Amino-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.500 g, 2.020 mmol), (Example 25: step c), triethylamine (0.153 g, 3.030 mmol), and DCM [30 mL] were added to a flask containing a stirbar. 4-Methanesulfonyl-butyryl chloride (0.013 g, 0.611 mmol) was added slowly while monitoring reaction. Reaction was concentrated in vacuo followed by chromatography (50%–80% EtOAc/Hx). Material was dissolved in a solution of trifluoroacetic acid/dichloromethane (1:1), [4 mL]. This solution stirred at room temperature for 2 hours. Reaction was concentrated in vacuo followed by reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to yield title compound (0.138 g, 88%). ESI-MS (m/z): Calcd. for C24H27N3O5S4: 566.75; found 566.1.

Workup

  1. additioncontaining a stirbar
  2. customreaction
  3. customReaction
  4. concentrationwas concentrated in vacuo
  5. dissolutionMaterial was dissolved in a solution of trifluoroacetic acid/dichloromethane (1:1), [4 mL]
  6. customReaction
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-d694010096e5442491f8671320da781c
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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