Benzenesulfonyl chloride, 2,4-dichloro- → HCID 59864866, compound

HRID 2423314Notes

Reaction equation

HRID 2423314 reaction equation
[NH2:1][C:2]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]C)=[O:20])=[CH:14][C:13]=2[Cl:23])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:24])[NH:6]2.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[Cl:23][C:13]1[CH:14]=[C:15]([CH2:18][C:19]([OH:21])=[O:20])[CH:16]=[CH:17][C:12]=1[O:11][C:10]1[C:2]([NH:1][S:33]([C:27]2[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=2[Cl:25])(=[O:35])=[O:34])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5](=[O:24])[CH2:4]2

Participants

4

Reactant 2

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 59864792HCID 59864792, compound

Product 1

HCID 59864866HCID 59864866, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

23.2 (35 mg, 0.1 mmol) and 2,4-dichlorobenzenesulfonyl chloride (52 mg, 0.21 mmol) were stirred in pyridine (0.5 mL) at 25° C. for 4 h. The reaction mixture was loaded directly to a prepacked Redisep Column and flash chromatographed (gradient, 0-100% EtOAc in Hexanes) to give the sulfonamide, which was then hydrolyzed in MeOH/THF/water (0.3 mL each) with LiOH (7 mg, 0.3 mmol) at 25° C. for 2 h. Reverse phase HPLC (C18, 10-90% ACN in water with 0.1% TFA as eluant) of the reaction mixture afforded 23 as a yellow solid. MS ESI (pos.) m/e calcd for (M+H)+ 543.0.1. found 543.0. 1H NMR (500 MHz) (CDCl3) δ 12.45 (br. s, 1H); 10.47 (s, 1H); 10.08 (s, 1H); 7.73 (d, J=8.5 Hz, 1H); 7.58 (s, 1H); 7.34 (d, J=8.5 Hz, 1H); 7.33 (s, 1H); 7.04 (d, J=7.8, 1H); 6.71 (d, J=8.3 Hz, 1H); 6.54 (d, J=8.1 Hz, 1H); 6.43 (d, J=8.3 Hz, 1H); 3.57 (s, 2H); 3.56 (s, 2H).

Workup

  1. customchromatographed (gradient, 0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-3ad4dcca4151425bbac8c35c0e4602a2
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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