1-Hydroxybenzotriazole → HCID 25165531, compound

HRID 1178152Notes

Reaction equation

HRID 1178152 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:26]2[O:30][N:29]=[C:28]([C:31]([OH:33])=O)[CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:66])[C:58]2[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=2[Cl:65])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[Cl:65][C:59]1[CH:60]=[CH:61][C:62]([Cl:64])=[CH:63][C:58]=1[C:57]([N:54]1[CH2:53][CH2:52][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:31]([C:28]2[CH:27]=[C:26]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:30][N:29]=2)=[O:33])[CH2:56][CH2:55]1)=[O:66]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1519165-Phenyl-3-isoxazolecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66953488HCID 66953488, compound

Product 1

HCID 25165531HCID 25165531, compoundYield 53.39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (24 mg, 0.18 mmol) and DIPEA (74 mg, 0.57 mmol) were added to a stirred solution of 5-phenyl-isoxazole-3-carboxylic acid (27 mg, 0.14 mmol) in DMF (1.0 mL). The mixture was then cooled to 10° C. and EDCI.HCl (34 mg, 0.18 mmol) followed by 2-amino-1-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-ethanone hydrochloride (50 mg, 0.15 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Water was added, and the resulting precipitate was isolated by filtration under reduced pressure and dried in vacuo to afford 5-phenyl-isoxazole-3-carboxylic acid {2-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide as a solid 53.39% yield. LC-MS purity: 92.758%. 1H-NMR (DMSO): δ 8.78 (t, 1H), 8.0 (m, 2H), 7.6 (m, 6H), 7.47 (s, 1H), 4.2 (m, 2H), 3.8 (m, 1H), 3.7 (m, 2H), 3.56 (m, 2H), 3.2 (m, 3H).

Workup

  1. additionwere added
  2. customthe resulting precipitate was isolated by filtration under reduced pressure
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f27fcf0d010048bfa9d7717f0f97ab85
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…