Ethanesulfonylchloride, 2-chloro- → HCID 58367160, compound

HRID 1891478Notes

Reaction equation

HRID 1891478 reaction equation
Cl.[NH2:2][C@@H:3]1[C:11]2[C:6](=[C:7]([C:12]3[S:16][C:15]([C:17]4[CH:18]=[CH:19][C:20]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=4)[C:22]#[N:23])=[N:14][N:13]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.Cl[CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:16][C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[CH2:5][CH2:4][C@@H:3]4[NH:2][S:32]([CH:31]=[CH2:30])(=[O:34])=[O:33])=[N:13][N:14]=2)[CH:18]=[CH:19][C:20]=1[O:25][CH:26]([CH3:28])[CH3:27])#[N:23]

Participants

4

Reactant 2

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 67193845(S)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride

Product 1

HCID 58367160HCID 58367160, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (5)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride 4 (40 mg, 0.5 mmol) and TEA (49 mg, 0.48 mmol) in DCM (2 mL) was added 2-chloroethanesulfonyl chloride (79 mg, 0.48 mmol) at 0° C. The reaction was warmed to room temperature and stirred for 2 h. The reaction was quenched by the addition of NaHCO3. The product was purified by chromatography (EA/hexane) to provide 30 mg (66%) of (S)-N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)ethenesulfonamide as yellow solid. LCMS-ESI (m/z) calculated for C23H22N4O3S2: 466.1; found 467.1 [M+H]+, tR=3.63 min.

Workup

  1. customThe reaction was quenched by the addition of NaHCO3
  2. customThe product was purified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-23aa10705fb148edb2f12847f76e0f45
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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