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1-Hydroxybenzotriazole → HCID 178523552, compound

HRID 1178146
Notes
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Reaction equation

HRID 1178146 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595595982-Amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanoneHCID 178479739HCID 178479739, compound

Product 1

HCID 178523552
HCID 178523552, compound
Yield 26.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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

  1. filtrationthe resulting precipitate was filtered
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes