Cesium carbonate → 4-{4-Nitro-3-[(2-phenoxy-acetyl)-(4-trifluoromethoxy-benzyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 131206Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([NH:23][C:24](=[O:33])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:40][C:41]([F:52])([F:51])[O:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47]Br)=[CH:45][CH:44]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([N:23]([C:24](=[O:33])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:47][C:46]3[CH:49]=[CH:50][C:43]([O:42][C:41]([F:40])([F:51])[F:52])=[CH:44][CH:45]=3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1 g (2.19 mmol) 4-[4-nitro-3-(2-phenoxy-acetylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester, 1.07 g (3.29 mmol) cesiumcarbonate and 0.79 g (3.29 mmol) 4-(trifluoromethoxy)benzyl bromide (commercially available) in 6.6 ml DMF was stirred at 110° C. for 2 h. After cooling to room temperature the precipitate was filtered of. The residue was used without further purification. The title compound was isolated as brown solid (0.39 g; 37%). MS(ISP): 631.5 (M+H)+

Workup

temperatureAfter cooling to room temperature the precipitate
filtrationwas filtered of
customThe residue was used without further purification

Sources & evidence

ORD record: ord-7c1fa1b52cab46979e015c55238d1519
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384945B2

Reaction notes

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