2-Dimethylaminopyridine → HCID 70983531, compound

HRID 625928Notes

Reaction equation

HRID 625928 reaction equation
[Cl-].[CH2:2]([CH:9]1[C:15]2[CH:16]=[C:17]([O:20][CH2:21][CH2:22][NH3+:23])[CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][CH2:11][N:10]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C1C=CC=CN=1)C.[CH3:38][N:39]1[CH:43]=[C:42]([S:44](Cl)(=[O:46])=[O:45])[N:41]=[CH:40]1>ClCCl.C(OCC)(=O)C>[CH2:2]([CH:9]1[C:15]2[CH:16]=[C:17]([O:20][CH2:21][CH2:22][NH:23][S:44]([C:42]3[N:41]=[CH:40][N:39]([CH3:38])[CH:43]=3)(=[O:46])=[O:45])[CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][CH2:11][N:10]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 70982639HCID 70982639, compound

Product 1

HCID 70983531HCID 70983531, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.12 mmol 2-(1-benzyl-2-(ethoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yloxy)ethanaminium chloride in 3 ml dichloromethane were added 0.33 mmol dimethylaminopyridine and 0.17 mmol 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature over night. The mixture was diluted with ethyl acetate and washed with NH4Cl solution (2×), water (1×), and brine (1×). The organic layer was dried over MgSO4 and filtered. Evaporation of the solvent gave 66 mg of crude material that was purified by flash chromatography to yield 60 mg of ethyl 1-benzyl-8-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-4,5-dihydro-1H-benzo[c]azepine-2(3H)carboxylate (95%).

Workup

  1. washwashed with NH4Cl solution (2×), water (1×), and brine (1×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customEvaporation of the solvent
  5. customgave 66 mg of crude material that
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-86e2f3db182a47ebbe3e5a3993ac981d
Source dataset
uspto-grants-2016_04
Patent number
US09309200B2

Reaction notes

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