Triethylamine → (2S)-3-(4-{[3-(2,3-dichlorophenyl)isoxazol-5-yl]methyl}piperazinyl)-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol

HRID 891060Notes

Reaction equation

HRID 891060 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].Cl[O-].[Na+].[CH3:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]([OH:38])[CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH2:35][C:36]#[CH:37])[CH2:31][CH2:30]3)=[CH:21][C:19]=2[N:20]=1.C(N(CC)CC)C>ClCCl.CO>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]1[CH:37]=[C:36]([CH2:35][N:32]2[CH2:33][CH2:34][N:29]([CH2:28][C@H:27]([OH:38])[CH2:26][O:25][C:22]3[CH:23]=[CH:24][C:18]4[S:17][C:16]([CH3:15])=[N:20][C:19]=4[CH:21]=3)[CH2:30][CH2:31]2)[O:6][N:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 718876N-[(2,3-dichlorophenyl)methylidene]hydroxylamineHCID 23665760Sodium HypochloriteHCID 58595329(2S)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ynylpiperazinyl)propan-2-ol

Product 1

HCID 58595332(2S)-3-(4-{[3-(2,3-dichlorophenyl)isoxazol-5-yl]methyl}piperazinyl)-1-(2-methylbenzothiazol-5-yloxy)propan-2-olYield 4.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2,3 dichlorobenzaldehyde oxime (136 mg, 0.725 mmol) in 1 ml of dichloromethane was added aqueous sodium hypochlorite solution (>4%, 1.35 ml, 0.725 mmol). The reaction was sealed in a reaction vessel with a stirbar. The vessel was subjected to microwave under the following conditions: temperature=60° C., time=240(s), high absorbance, fixed hold time=on, pre-stir=10(s). After 4 minutes (2S)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-ynylpiperazinyl)propan-2-ol (50 mg, 0.145 mmol) in 1 ml of dichloromethane was added, followed by triethylamine (0.022 ml, 0.145 mmol). The reaction vessel was again subjected to microwave under the following conditions: temperature=110° C., time=240(s), high absorbance, fixed hold time=on, pre-stir=10(s). After 4 minutes, thin layer chromatography (10:1 dichloromethane:methanol) showed consumption of starting material and product formation. The solution was evaporated under reduced pressure and purified by preparative thin layer chromatography (10:1 dichloromethane:methanol) followed by HPLC to yield (2S)-3-(4-{[3-(2,3-dichlorophenyl)isoxazol-5-yl]methyl}piperazinyl)-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol (20) (3.2 mg, M+1=533.21)

Workup

  1. customThe reaction was sealed in a reaction vessel with a stirbar
  2. customconsumption of starting material and product formation
  3. customThe solution was evaporated under reduced pressure
  4. custompurified by preparative thin layer chromatography (10:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-dc032fb284c34e55a905eaf097c98da9
Source dataset
uspto-grants-2006_02
Patent number
US07001909B2

Reaction notes

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