Dimethyl Sulfoxide → HCID 59420881, compound

HRID 499207Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.ClC(Cl)(Cl)CO[C:24](=[O:42])[NH:25][C:26]1[N:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37](C)(C)C)=[CH:33][C:32]=2C)[N:28]=[CH:29][CH:30]=1.C(N(CC)[CH:49]([CH3:51])[CH3:50])(C)C.[CH3:54]S(C)=O>>[C:49]([C:29]1[CH:30]=[C:26]([NH:25][C:24]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8](=[O:9])[C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)[CH2:4][CH2:3]2)=[O:42])[N:27]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)[N:28]=1)([CH3:51])([CH3:54])[CH3:50]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 81531Diisopropylethylamine

HCID 16772821(4-Amino-1-piperidinyl)[4-(methylsulfonyl)phenyl]methanone

HCID 68456462HCID 68456462, compound

Product 1

HCID 59420881HCID 59420881, compound

Conditions

Temperature: 60 °C

Procedure

Nitrogen gas is bubbled through a solution of (4-amino-piperidin-1-yl)-(4-methylsulfonyl-phenyl)-methanone (141.6 mg, 0.50 mmol) and (5-tert-butyl-2-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (204.8 mg, 0.51 mmol) in DMSO (2 mL) for 2 minutes. Next, N,N-diisopropylethylamine (0.20 mL) is added. The reaction mixture is stirred at 60° C. for 6 hours. The crude product is purified on a silica gel chromatography with ethyl acetate to give a white solid (261.2 mg, 97.2%, ES+(m/z) 538.3 [M+H]).

Workup

customThe crude product is purified on a silica gel chromatography with ethyl acetate
customto give a white solid (261.2 mg, 97.2%, ES+(m/z) 538.3 [M+H])

Sources & evidence

ORD record: ord-694ea1aa038345639aedbbd9a1e40b41
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767674B2

Reaction notes

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