1-Hydroxybenzotriazole → HCID 178488299, compound

HRID 1178153Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[C:21]1([C:27]2[NH:31][N:30]=[C:29]([C:32]([OH:34])=O)[CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.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:68])[C:59]2[CH:64]=[C:63]([O:65][CH3:66])[CH:62]=[CH:61][C:60]=2[Br:67])[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[Br:67][C:60]1[CH:61]=[CH:62][C:63]([O:65][CH3:66])=[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:32]([C:29]2[CH:28]=[C:27]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:31][N:30]=2)=[O:34])[CH2:57][CH2:56]1)=[O:68]

Participants

Conditions

Temperature: 10 °C

Procedure

HOBt (22 mg, 0.16 mmol) and DIPEA (66 mg, 0.51 mmol) were added to a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid hydrochloride (29 mg, 0.13 mmol) in DMF (1.0 mL). The mixture was then cooled to 10° C. and EDCI.HCl (30.5 mg, 0.16 mmol) followed by 2-amino-1-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-ethanone hydrochloride (50 mg, 0.13 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Water was added, and the resulting precipitate was isolated by filtration. The crude product was washed with hexane and diethyl ether to afford 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-5-methoxy-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide as a solid in 59% yield. LC-MS purity: 89.83%, 1H-NMR (DMSO): δ 8.62 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.58 (m, 1H), 7.5 (m, 2H), 7.4 (m, 1H), 7.1 (s, 1H), 7.0 (m, 2H), 4.2 (m, 2H), 3.8 (s, 3H), 3.75 (m, 2H), 3.6 (m, 2H), 3.55 (m, 2H), 3.2 (m, 2H).

Workup

additionwere added
customthe resulting precipitate was isolated by filtration
washThe crude product was washed with hexane and diethyl ether

Sources & evidence

ORD record: ord-8e9317010fda476faec5978f513c661d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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