Diisopropylethylamine → tert-butyl 4-{3-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperazine-1-carboxylate

HRID 1818838Notes

Reaction equation

HRID 1818838 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[S:6]1(=[O:23])=[O:22].[N:24]1([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)C>[F:21][C:16]1[CH:15]=[C:14]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:5]([CH2:4][CH2:3][CH2:2][N:27]3[CH2:26][CH2:25][N:24]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:29][CH2:28]3)[S:6]2(=[O:23])=[O:22])[CH:19]=[CH:18][C:17]=1[F:20]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 687126561-(3-Bromopropyl)-3-(3,4-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 68709886tert-butyl 4-{3-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperazine-1-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-bromopropyl)-3-(3,4-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.2, 0.5 mmol) in anhydrous dimethylformamide (3 mL) was treated with tert-butyl piperazine-1-carboxylate (0.19 g, 1 mmol) and N,N-diisopropylethylamine (0.17 mL, 1 mmol). The reaction mixture stirred at ambient for 48 h. The reaction mixture was diluted with ethyl ether (10 mL) and washed with H2O (2×10 mL), the organic layer was isolated, dried with MgSO4 and evaporated. The crude reaction product was purified by flash chromatography (SiO2, 3-50% ethyl acetate/hexane) to provided tert-butyl 4-{3-[3-(3,4-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperazine-1-carboxylate (0.17 g, 67%) as a white solid:

Workup

  1. washwashed with H2O (2×10 mL)
  2. customthe organic layer was isolated
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. customThe crude reaction product
  6. customwas purified by flash chromatography (SiO2, 3-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7a3dfb16a9b147879c275892cfd781e9
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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