Triethylamine → HCID 21023601, compound

HRID 1795030Notes

Reaction equation

HRID 1795030 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.Cl[O-].[Na+].[CH3:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:37])[CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH2:34][CH:35]=[CH2:36])[CH2:30][CH2:29]3)=[CH:20][C:18]=2[N:19]=1.C(N(CC)CC)C>ClCCl.CO>[CH3:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C@H:26]([OH:37])[CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH2:34][CH:35]4[O:1][N:2]=[C:3]([C:4]5[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=5)[CH2:36]4)[CH2:30][CH2:29]3)=[CH:20][C:18]=2[N:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 19475HCID 19475, compoundHCID 22184716HCID 22184716, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 21023601HCID 21023601, compoundYield 5.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of (hydroxyimino)(4-methylphenyl)methane (97 mg, 0.72 mmol) in 1 ml of dichloromethane was added aqueous sodium hypochlorite solution (>4%, 1.33 ml, 0.72 mmol). The reaction mixture was stirred at room temperature for 30 minutes, after which time TLC (20:1 dichloromethane:methanol) showed conversion of oxime to chlorinated oxime (17). 1-(2-Methylbenzothiazol-5-yloxy)-3-(4-prop-2-enylpiperazinyl)propan-2-ol (50 mg, 0.144 mmol) in 0.5 ml of dichloromethane and triethylamine (0.022 ml, 0.145 mmol) were added. The reaction was stirred at room temperature overnight. Thin layer chromatography (10:1 dichloromethane:methanol) showed consumption of starting material and product formation. The solution was evaporated under reduced pressure, and the residue purified by preperative HPLC, to yield (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-{[3-(4-methylphenyl)(4,5-dihydroisoxazol-5-yl)]methyl}piperazinyl)propan-2-ol (3.6 mg, M+1=481.35)

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customconsumption of starting material and product formation
  3. customThe solution was evaporated under reduced pressure
  4. customthe residue purified by preperative HPLC

Sources & evidence

ORD record
ord-0ff74220f6434104bdd697512ca31e66
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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