Benzenamine, 4-(4-morpholinyl)- → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-N-(4-morpholin-4-yl-phenyl)-3-oxo-propionamide

HRID 1665658Notes

Reaction equation

C1C=CC2N(O)N=NC=2C=1.[Br:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:27])[CH2:23][C:24]([OH:26])=O)[CH2:18][CH2:17]1)=[O:15].CCN=C=NCCCN(C)C.Cl.[N:44]1([C:50]2[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Br:11][C:12]1[CH:31]=[CH:30][CH:29]=[CH:28][C:13]=1[C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22](=[O:27])[CH2:23][C:24]([NH:56][C:53]2[CH:52]=[CH:51][C:50]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:55][CH:54]=2)=[O:26])[CH2:20][CH2:21]1)=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

HOBt (31 mg, 0.23 mmol) and DMAP (42 mg, 0.34 mmol) were added to a stirred solution of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid (75 mg, 0.2 mmol) in DMF (1 mL). The reaction mixture was cooled to 0° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by 4-morpholin-4-yl-phenylamine (41 mg, 0.23 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water. The resulting precipitate was filtered and washed with hexane to afford 45 mg (41%) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-N-(4-morpholin-4-yl-phenyl)-3-oxo-propionamide. LCMS: 516.12 (M+1)+, 97.57%, 1H NMR: (DMSO-d6): δ 7.7 (m, 1H), 7.5-7.32 (m, 5H), 6.9-6.8 (m, 2H), 3.8-3.7 (bs, 5H), 3.6-3.4 (m, 7H), 3.2-3.08 (m, 2), 3.04-2.98 (m, 3H).

Workup

additionwere added
filtrationThe resulting precipitate was filtered
washwashed with hexane

Sources & evidence

ORD record: ord-871d2e16c05844c7b55502129f185a40
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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