1-Hydroxybenzotriazole → HCID 178523552, compound

HRID 1178146Notes

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.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:69])[C:58]2[CH:63]=[C:62]([F:64])[CH:61]=[CH:60][C:59]=2[C:65]([F:68])([F:67])[F:66])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[F:64][C:62]1[CH:61]=[CH:60][C:59]([C:65]([F:67])([F:66])[F:68])=[C:58]([CH:63]=1)[C:57]([N:54]1[CH2:55][CH2:56][N:51]([C:49](=[O:50])[CH2:48][NH:47][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])[CH2:52][CH2:53]1)=[O:69]

Participants

Conditions

Temperature: 10 °C

Procedure

HOBt (38 mg, 0.28 mmol) and DIPEA (145 mg, 1.12 mmol) were added to a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid hydrochloride (51 mg, 0.22 mmol) in DMF (1.0 mL). The reaction mass was cooled to 10° C., and EDCI.HCl (54 mg, 0.28 mmol) was added, followed by the addition of 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (100 mg, 0.22 mmol). The resulting mixture was stirred at room temperature overnight. The mixture was then diluted with water and the resulting precipitate was filtered and dried under reduced pressure to afford 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide as a solid in 26.8% yield, LC-MS purity: 96.054%, 1H NMR (DMSO): δ 8.1 (s, 1H), 7.95 (s, 1H), 7.8 (d, 2H), 7.56 (m, 2H), 7.5 (t, 2H), 7.4 (m, 1H), 7.1 (s, 1H) 4.2 (m, 2H), 3.75 (m, 1H), 3.6 (m, 4H), 3.5 (m, 2H), 3.2 (m, 2H), 3.1 (s, 1H).

Workup

filtrationthe resulting precipitate was filtered
customdried under reduced pressure

Sources & evidence

ORD record: ord-9f62116c499047c5b76fb081e84832ac
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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