Diisopropylethylamine → rac-cis-(5-(4-Fluorophenyl)-2-methylthiazol-4-yl)(2-(((4-methoxypyrimidin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)methanone

HRID 60799

Reaction equation

[NH2:1][CH2:2][C@H:3]1[C@@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[N:13]=[C:14]([CH3:24])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:11].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29](Cl)[N:28]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]2[S:15][C:14]([CH3:24])=[N:13][C:12]=2[C:10]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:8]([CH3:9])[C@@H:3]2[CH2:2][NH:1][C:29]2[N:28]=[C:27]([O:26][CH3:25])[CH:32]=[CH:31][N:30]=2)=[O:11])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of rac-cis-(2-(aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone, 4-methoxy-2-chloropyrimidine, and DIPEA in isopropanol was stirred at 110° C. for 18 h. The reaction was cooled and concentrated in vacuo. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 456.02 (M+H).

Workup

temperatureThe reaction was cooled
concentrationconcentrated in vacuo
customThe crude reaction mixture
customwas purified by reverse-phase preparative HPLC

Sources & evidence

ORD record: ord-1d3c11367f7b4f488f0b06069359f832
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Linked notes

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