Dichloromethane → HCID 67495117, compound
Reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.ON1C2N=CC=CC=2N=N1.ClCCl.[Br:46][C:47]1[CH:53]=[CH:52][C:50]([NH2:51])=[CH:49][CH:48]=1.C(N(CC)C(C)C)(C)C>>[Br:46][C:47]1[CH:53]=[CH:52][C:50]([NH:51][C:16](=[O:17])[C:15]2[CH:14]=[CH:13][C:12]([N:9]3[CH2:10][CH2:11][N:6]([C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])[CH2:7][CH2:8]3)=[CH:20][CH:19]=2)=[CH:49][CH:48]=1Participants
7
Procedure
A solution of 4-(4-cyclopropanecarbonyl-piperazin-1-yl)-benzoic acid (1.0 g, 3.6 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.70 g, 3.6 mmol) and 1-hydroxy-7-azabenzotriazole (0.50 g, 3.6 mmol) in dichloromethane (39 mL, 610 mmol) was stirred for 20 min at room temperature and then p-bromoaniline (0.52 g, 3.0 mmol) and N,N-diisopropylethylamine (2.6 mL, 15 mmol) were added and the reaction mixture was stirred for 2 days. The reaction mixture was filtered; the filtrate was dissolved in 1:1 acetic acid:water (8 mL). A precipitate formed. This material was filtered to provide the title product as the acetic acid salt (225 mg). (m/z): [M+H]+ calcd for C21H22BrN3O2 428.09 found 428.0.
Workup
- filtrationThe reaction mixture was filtered
- dissolutionthe filtrate was dissolved in 1:1 acetic acid
- customA precipitate formed
- filtrationThis material was filtered
Sources & evidence
- ORD record
- ord-c42f9a4981674d458f0aa6a2bc40578c
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921372B2
Reaction notes
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