2,5-Dichlorobenzenesulfonyl chloride → HCID 57732809, compound

HRID 1806478Notes

Reaction equation

HRID 1806478 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH:6]=[CH:7][CH:8]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=1[S:40](Cl)(=[O:42])=[O:41].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=1[S:40]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[C:16]([C:18]([NH2:20])=[O:19])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:21]2[CH2:22][CH2:23][N:24]([S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[CH2:25][CH2:26]2)[CH:6]=[CH:7][CH:8]=1)(=[O:42])=[O:41]

Participants

6

Reactant 3

HCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 16038109HCID 16038109, compound

Product 1

HCID 57732809HCID 57732809, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[3-(aminomethyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (40 mg, 0.096 mmol) in DMF (1.0 mL) and DCM (1.0 mL) was added 2,5-dichlorobenzenesulfonyl chloride (86 mg, 0.352 mmol) and DIEA (62 μL, 0.352 mmol). Reaction was stirred at room temperature for 6 h. Reaction mixture was then concentrated and purified by Gilson Preparatory HPLC to give 6.6 mg the title compound (11%). LC/MS=m/z 649.2 [M+H] Ret. Time: 2.25 min

Workup

  1. customReaction
  2. customReaction mixture
  3. concentrationwas then concentrated
  4. custompurified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-5025082e6ee44ee8be3d27fc3d6bcfdb
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

Loading…