Ammonia → HCID 67374395, compound

HRID 1676977Notes

Reaction equation

HRID 1676977 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25](Cl)(=[O:27])=[O:26].CCOC(C)=O.[NH3:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25]([NH2:35])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 67374395HCID 67374395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Through a 0° C. solution of the product from Example 1, Step C (96 mg, 0.21 mmols) in 5 mL of CH2Cl2, ammonia gas was bubbled for 3 minutes. The reaction was sealed, stirred for 30 minutes, warmed to room temperature and stirred 20 minutes more. This was poured into EtOAc and washed with water and brine. The solution was dried over Na2SO4 and concentrated in vacuo to give the titled compound. ESI+MS: 443 [M+H]+.

Workup

  1. customThe reaction was sealed
  2. stirringstirred 20 minutes more
  3. washwashed with water and brine
  4. dry with materialThe solution was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4a6005b7be24ff9a67f4a9f4379f64c
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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