Water → (S)-2-(1-methylethylsulfonamido)-N-(2-(methylsulfonamido)phenyl)-2,3-dihydro-1H-indene-5-carboxamide

HRID 473113Notes

Reaction equation

HRID 473113 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17].[CH3:20][CH:21]([S:23]([NH:26][C@@H:27]1[CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:36](Cl)=[O:37])[CH:33]=2)[CH2:28]1)(=[O:25])=[O:24])[CH3:22].O>C(Cl)Cl>[CH3:22][CH:21]([S:23]([NH:26][C@@H:27]1[CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:36]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[O:37])[CH:33]=2)[CH2:28]1)(=[O:25])=[O:24])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 241357N-(2-aminophenyl)methanesulfonamideHCID 86668751(S)-2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carbonyl chloride

Product 1

HCID 66736340(S)-2-(1-methylethylsulfonamido)-N-(2-(methylsulfonamido)phenyl)-2,3-dihydro-1H-indene-5-carboxamideYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of triethylamine (0.083 mmol, 0.012 mL, 8.38 mg) and N-(2-aminophenyl)methanesulfonamide (0.083 mmol, 15.43 mg) in DCM (2 mL) was added to a solution of (S)-2-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carbonyl chloride (0.083 mmol, 25 mg) in DCM (1 mL) was added. The reaction mixture was stirred at room temp overnight. H2O was added and the reaction mixture filtered through a hydrophobic frit and the DCM layer was concentrated under reduced pressure. The residue was purified by prep-HPLC to give desired product (10.7 mg, 28.6%). MS (ESI): m/z [M−H]− 450.2

Workup

  1. additionwas added
  2. filtrationthe reaction mixture filtered through a hydrophobic frit
  3. concentrationthe DCM layer was concentrated under reduced pressure
  4. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-25b2277f54a14d6db35d1545468b4e04
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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