1-Hydroxybenzotriazole → HCID 44230805, compound

HRID 1665593Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:32])[CH2:28][C:29]([OH:31])=O)=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl.[Cl:52][C:53]1[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][C:54]=1[C:60]([N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)=[O:61]>CN(C=O)C.O>[C:20]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:32])[CH2:28][C:29]([N:65]2[CH2:66][CH2:67][N:62]([C:60](=[O:61])[C:54]3[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:53]=3[Cl:52])[CH2:63][CH2:64]2)=[O:31])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 10 °C

Procedure

HOBt (25 mg, 0.185 mmol) and DIPEA (22 mg, 0.175 mmol) were added to a stirred solution of N-biphenyl-4-yl-malonamic acid (50 mg, 0.175 mmol) in DMF (3 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (50 mg, 0.26 mmol) was added followed by the addition of (2,5-dichloro-phenyl)-piperazin-1-yl-methanone hydrochloride (55 mg, 0.187 mmol). The reaction mixture was stirred at room temperature overnight. Water was then added and the resulting precipitate was filtered and purified by column chromatography using silica gel 60-120 mesh and 50% ethyl acetate in hexane as eluant to afford 35 mg (41%) of N-biphenyl-4-yl-3-[4-(2,5-dichloro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 497.11 M+1)+, 95.5%. 1H NMR: (CDCl3): δ 9.6 (d, 1H), 7.64 (m, 2H), 7.58 (m, 4H), 7.44 (m, 3H), 7.38 (d, 2H), 7.32 (m, 2H), 3.95 (m, 2H), 3.8 (m, 1H), 3.75 (m, 4H), 3.65 (m, 1H), 3.52 (d, 3H), 3.34 (m, 3H).

Workup

filtrationthe resulting precipitate was filtered
custompurified by column chromatography

Sources & evidence

ORD record: ord-d6d6076eb64a43b8924c0bd271098dfb
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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