Hydrochloric Acid → HCID 178523546, compound

HRID 1178154Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:26]2[NH:30][N:29]=[C:28]([C:31]([OH:33])=O)[CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.CCN=C=NCCCN(C)C.Cl.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][N:55]([C:58](=[O:67])[C:59]2[CH:64]=[C:63]([Cl:65])[CH:62]=[CH:61][C:60]=2[Cl:66])[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[Cl:66][C:60]1[CH:61]=[CH:62][C:63]([Cl:65])=[CH:64][C:59]=1[C:58]([N:55]1[CH2:54][CH2:53][N:52]([C:50](=[O:51])[CH2:49][NH:48][C:31]([C:28]2[CH:27]=[C:26]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:30][N:29]=2)=[O:33])[CH2:57][CH2:56]1)=[O:67]

Participants

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-1H-pyrazole-3-carboxylic acid; hydrochloride (32 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, 0.14 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Water was added, and the resulting precipitate was isolated by filtration and dried under reduced pressure to afford 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide as a solid in 89.47% Yield. LC-MS purity: 92.226%. 1H-NMR (DMSO): δ 8.6 (s, 1H), 8.1 (t, 1H), 7.8 (m, 2H), 7.6 (m, 3H), 7.45 (m, 4H), 7.1 (s, 1H), 3.9 (m, 2H), 3.4 (m, 6H), 3.2 (m, 2H).

Workup

additionwere added
customthe resulting precipitate was isolated by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-0c584be4c79848008df0208823d16002
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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