Triethylamine → HCID 67370750, compound

HRID 1676996Notes

Reaction equation

HRID 1676996 reaction equation
[Br: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].[C:29]([NH:36][CH2:37][CH2:38][NH2:39])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(N(CC)CC)C.CCOC(C)=O>C(Cl)Cl>[Br: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]([NH:39][CH2:38][CH2:37][NH:36][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 187201N-BOC-ethylenediamineHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 67370750HCID 67370750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 3, Step A (400 mg, 0.789 mmols) in 5 mL of CH2Cl2, Boc-ethylenediamine (0.137 mL, 0.868 mmol) and triethylamine (0.22 mL, 1.6 mmol) were added. The reaction stirred at room temperature for 2 days, then poured into EtOAc, washed with saturated NaHCO3 solution and brine. The solution was dried over Na2SO4 and concentrated in vac o. Purification by flash chromatograpy using EtOAc:hexane (1:3) gave the titled compound. ESI+ MS: 530 [MH-Boc]+.

Workup

  1. washwashed with saturated NaHCO3 solution and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. concentrationconcentrated in vac o
  4. customPurification by flash chromatograpy

Sources & evidence

ORD record
ord-bf6ccc47753043a68e7b5af994ad7448
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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