1-Methyl-1H-imidazole-2-sulfonyl chloride → ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-2-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 587879Notes

Reaction equation

HRID 587879 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[CH:11]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1.[CH3:27][N:28]1[CH:32]=[CH:31][N:30]=[C:29]1[S:33](Cl)(=[O:35])=[O:34]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:14]([CH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([O:4][CH2:3][CH2:2][NH:1][S:33]([C:29]3[N:28]([CH3:27])[CH:32]=[CH:31][N:30]=3)(=[O:35])=[O:34])[CH:13]=2)[CH2:9][CH:10]1[NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 116583831-Methyl-1H-imidazole-2-sulfonyl chlorideHCID 66740622Ethyl 6-(2-aminoethoxy)-1-benzyl-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 66740359ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-2-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 6-(2-aminoethoxy)-1-benzyl-2,3-dihydro-1H-inden-2-ylcarbamate (44.7 mg, 0.126 mmol; see example 193.8) in dry dichloromethane (2 ml) was added 4-dimethylaminopyridine (18.49 mg, 0.151 mmol) followed by 1-methyl-1H-imidazole-2-sulfonyl chloride (22.78 mg, 0.126 mmol). The reaction mixture was stirred at room temperature for 1 h. Added dichloromethane and washed twice with 1N hydrochloric acid. The collected organic layers were washed with water, sodium bicarbonate and brine, dried, filtered and evaporated to obtain ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-2-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate as a white foam. m=60 mg (95%)

Workup

  1. washAdded dichloromethane and washed twice with 1N hydrochloric acid
  2. washThe collected organic layers were washed with water, sodium bicarbonate and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-343ca590456e4487912c7a9ecc256807
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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