1-Hydroxybenzotriazole → HCID 44230952, compound

HRID 1665604Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[C:27]([F:31])=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.Cl.[C:45]1([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:50]=[CH:49][C:48]([NH:51][C:52](=[O:62])[CH2:53][C:54](=[O:61])[N:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)=[CH:47][CH:46]=1>CN(C=O)C.O>[C:45]1([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:46]=[CH:47][C:48]([NH:51][C:52](=[O:62])[CH2:53][C:54]([N:55]2[CH2:56][CH2:57][N:58]([C:23](=[O:25])[C:22]3[CH:26]=[C:27]([F:31])[C:28]([Cl:30])=[CH:29][C:21]=3[Cl:20])[CH2:59][CH2:60]2)=[O:61])=[CH:49][CH:50]=1

Participants

Conditions

Temperature: 10 °C

Procedure

HOBt (23 mg, 0.17 mmol) and DIPEA (44.8 mg, 0.35 mmol) were added to a stirred solution of 2,4-dichloro-5-fluorobenzoic acid (29 mg, 0.14 mmol) in DMF (1 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (33 mg, 0.17 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (50 mg, 0.14 mmol) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water. The resulting precipitate was filtered to afford 50 mg (70%) of N-biphenyl-4-yl-3-[4-(2,4-dichloro-5-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 514.11 (M+1)+ 100%. 1H NMR: (CDCl3): δ 9.6 (d, 1H), 7.6 (m, 7H), 7.44 (t, 2H), 7.34 (t, 1H), 7.14 (d, 1H), 3.96 (bs, 2H), 3.72 (m, 4H), 3.54 (d, 2H), 3.34 (m, 2H).

Workup

additionwere added
filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-8d8ab8c841134a1d93b94558d90ea11b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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