Diisopropylethylamine → HCID 59420874, compound

HRID 499204Notes

Reaction equation

[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.ClC(Cl)(Cl)C[O:28][C:29](=O)[NH:30][C:31]1[N:32]([CH3:40])[N:33]=[C:34]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[C:36]([C:34]1[CH:35]=[C:31]([NH:30][C:29]([NH:1][C:2]2[CH:24]=[CH:23][C:5]([O:6][CH:7]3[CH2:8][CH2:9][N:10]([C:13](=[O:14])[C:15]4[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:22])[CH2:11][CH2:12]3)=[CH:4][CH:3]=2)=[O:28])[N:32]([CH3:40])[N:33]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

Conditions

Temperature: 60 °C

Procedure

Nitrogen gas is bubbled through a solution of [4-(4-amino-phenoxy)-piperidin-1-yl]-(2,6-dichlorophenyl)-methanone (47 mg, 0.12 mmol) and (5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (42 mg, 0.12 mmol) in DMSO (1.5 mL) for 5 min. Next, N,N-diisopropylethylamine (40 μL, 0.24 mmol) is added. The reaction mixture is stirred at 60° C. for 6 hours. Then, DMSO is removed by passing the reaction mixture through an SCX column. The crude product is obtained by eluting the SCX column with 2M ammonia in methanol and purifying the residue on silica gel with ethyl acetate-hexanes (25%) to give a white solid (ES+(m/z) 544.2 [M+H]).

Workup

customThen, DMSO is removed

Sources & evidence

ORD record: ord-a28c040660d3487b983b048ccba1ef84
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767674B2

Reaction notes

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