Triethylamine → 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one

HRID 1710654Notes

Reaction equation

HRID 1710654 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][C:11]([OH:13])=O)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.Cl.Cl.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][C:20]=1[O:31][CH3:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:11](=[O:13])[CH2:10][N:6]3[C:5]4[CH:14]=[CH:15][C:2]([OH:1])=[CH:3][C:4]=4[O:8][C:7]3=[O:9])[CH2:29][CH2:30]2)=[CH:21][C:20]=1[O:31][CH3:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 58834368(6-Hydroxy-2-oxo-benzooxazol-3-yl)-acetic acidHCID 671038731-(4-Chloro-3-methoxyphenyl)piperazine dihydrochloride

Product 1

HCID 588343493-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (6-hydroxy-2-oxo-benzooxazol-3-yl)-acetic acid (53) (800 mg, 1 equiv), 1-(4-chloro-3-methoxy-phenyl)-piperazine dihydrochloride (1.16 g, 1 equiv), BOP (1.7 g, 1 equiv), triethylamine (5 mL, 5 equiv) in 10 ml of DMF was stirred at room temperature for overnight. The resultant solution was then diluted with EtOAc (50 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated in vacuo to provide a crude residue which was purified by flash chromatography to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one (54).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto provide a crude residue which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3c319090d0d64ba0834243b68b94c5e1
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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