1-Propanesulfonyl chloride → HCID 71114478, compound

HRID 710169Notes

Reaction equation

HRID 710169 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[N:16][C:15]=3[CH:25]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH2:26]([S:29](Cl)(=[O:31])=[O:30])[CH2:27][CH3:28].C(Cl)Cl.O>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH:19]4[CH2:24][CH2:23][N:22]([S:29]([CH2:26][CH2:27][CH3:28])(=[O:31])=[O:30])[CH2:21][CH2:20]4)=[N:16][C:15]=3[CH:25]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 21908982Water methylene chlorideHCID 71089548HCID 71089548, compound

Product 1

HCID 71114478HCID 71114478, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 25 (80 mg, 0.24 mmol) was dissolved in DCM (10 ml) and added TEA (35 mg, 0.35 mmol). This mixture was stirred at rt for 15 mins Reaction mixture cooled to 0° C. and added propane-1-sulphonylchloride (33 mg, 0.23 mmol). Reaction mixture stirred at rt for 2 h. Work up (DCM/H2O) afforded the crude product. Crude was purified by column chromatography on 60-120 mesh silica gel using a gradient mixture of EtOAC and Petether (70:30) as eluent to afford the titled compound (8 mg) as a white solid. M.P.: 222-225° C. 1H-NMR NMR (δ ppm, DMSO-d6, 400 MHz): 8.09 (d, J 1.3, 1H), 7.82-7.72 (m, 3H), 7.71-7.61 (m, 4H), 3.67-3.58 (m, 2H), 3.30-3.22 (m, 2H), 3.09-2.99 (m, 2H), 2.25-2.16 (m, 2H), 1.92-1.79 (m, 2H), 1.69 (hextet, J 7.6, 2H), 0.98 (t, J 7.4, 3H).

Workup

  1. customReaction mixture
  2. temperaturecooled to 0° C.
  3. customReaction mixture
  4. stirringstirred at rt for 2 h
  5. customafforded the crude product
  6. customCrude was purified by column chromatography on 60-120 mesh silica gel using
  7. additiona gradient mixture of EtOAC and Petether (70:30) as eluent

Sources & evidence

ORD record
ord-7fbd97089294471984a790a8728923a5
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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