1-(5-Chloro-2-methoxy-benzenesulfonyl)-piperazine → HCID 66801819, compound

HRID 528047Notes

Reaction equation

HRID 528047 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)[N:6]2[CH3:11].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:34][CH3:35])=[C:23]([S:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)(=[O:27])=[O:26])[CH:24]=1>C(O)(C)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:34][CH3:35])=[C:23]([S:25]([N:28]2[CH2:29][CH2:30][N:31]([C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[C:5]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[N:6]4[CH3:11])[CH2:32][CH2:33]2)(=[O:26])=[O:27])[CH:24]=1

Participants

4

Reactant 2

HCID 10713391-(5-Chloro-2-methoxy-benzenesulfonyl)-piperazineHCID 86711714HCID 86711714, compound

Product 1

HCID 66801819HCID 66801819, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 6-chloro-9-methyl-8-(1-methyl-1H-pyrazol-4-yl)-9H-purine (30 mg, 0.12 mmol), 1-(5-chloro-2-methoxyphenylsulfonyl)piperazine (43.6 mg, 0.15 mmol, Oakwood Products, Inc.), and triethylaminem (84.0 uL, 0.60 mmol) in isopropyl alcohol (2.0 mL) were heated to 80° C. for 16 hours. The resulting precipitate was collected by vacuum filtration, washed with ethanol (2 mL), water (2 mL) and diethyl ether (2 mL) and dried under reduced pressure, to give 29.6 mg (49% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 8.23 (s, 1H), 8.05 (s, 1H), 7.70 (dt, 2H), 7.27 (d, 1H), 3.95 (s, 3H), 3.88 (s, 3H), 3.83 (s, 3H), 3.31-3.25 (m, 4H). MS (EI) for C21H23ClN8O3S: 503.7 (MH+).

Workup

  1. filtrationThe resulting precipitate was collected by vacuum filtration
  2. washwashed with ethanol (2 mL), water (2 mL) and diethyl ether (2 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f996ba4dcc114270a2a0b3e4352e679d
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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