4-Fluorobenzoic Acid → N-biphenyl-4-yl-3-[4-(4-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

HRID 1665607Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.Cl.[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52](=[O:59])[N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:45][CH:44]=1>CN(C=O)C.O>[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:44]=[CH:45][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52]([N:53]2[CH2:54][CH2:55][N:56]([C:25](=[O:27])[C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:29][CH:28]=3)[CH2:57][CH2:58]2)=[O:59])=[CH:47][CH:48]=1

Participants

Conditions

Temperature: 10 °C

Procedure

HOBt (34 mg, 0.25 mmol) and DIPEA (67.9 mg, 0.51 mmol) were added to a stirred solution of 4-fluorobenzoic acid (29 mg, 0.21 mmol) in DMF (1.5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide.hydrochloride (75 mg, 0.2 mmol) were added. The reaction mixture was stirred at room temperature overnight, then diluted with water. The resulting precipitate was filtered to afford 90 mg (97%) of N-biphenyl-4-yl-3-[4-(4-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 446.18 (M+1)+, 97.9%. 1H NMR: (CDCl3): δ 9.8 (s, 1H), 7.6 (m, 6H), 7.44 (m, 3H), 7.34 (t, 1H), 7.14 (t, 2H), 3.7 (m, 10H).

Workup

additionwere added
filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-408f5e7300a840cab7178b45f088d549
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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