Acetonitrile → N-[(2,4-dichlorophenyl)methyl]-1-{4-[(2-hydroxyethyl)amino]-6-methyl-1,3,5-triazin-2-yl}-4-piperidinecarboxamide

HRID 1678449Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[O:16])[CH2:11][CH2:10]2)[N:3]=1.C(#N)C.C[O:31][CH2:32][CH2:33][NH2:34].CCN(C(C)C)C(C)C>CS(C)=O>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:15]([CH:12]1[CH2:11][CH2:10][N:9]([C:4]2[N:3]=[C:2]([NH:34][CH2:33][CH2:32][OH:31])[N:7]=[C:6]([CH3:8])[N:5]=2)[CH2:14][CH2:13]1)=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 10 mL reaction vial was added the 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide (50 mg, 0.121 mmol) and acetonitrile (0.754 mL) to give a white suspension. Then, [2-(methyloxy)ethyl]amine (0.105 mL, 1.206 mmol) and DIEA (0.063 mL, 0.362 mmol) were added. The reaction was heated for 1 h at 80° C. The reaction mixture was diluted with DMSO and purified by preparative HPLC to provide N-[(2,4-dichlorophenyl)methyl]-1-{4-[(2-hydroxyethyl)amino]-6-methyl-1,3,5-triazin-2-yl}-4-piperidinecarboxamide (46 mg, 0.078 mmol, 65%) as a white solid. MS (ES) m/e 439, 441 [M+H]+. 1H NMR (400 MHz, DMSO-D6) 8.5 (bs, 1H), □ 8.3 (bs, 1H), 7.7 (s, 1H), 7.4 (m, 1H), 7.3 (m, 1H), 4.7 (m, 2H), 4.3 (m, 2H), 3.8-3.3 (3H under H2O peak), 3.1 (m, 4H), 2.6 (m, 1H), 2.3 (s, 3H), 1.8 (m, 2H), 1.5 (m, 2H)

Workup

customTo a 10 mL reaction
customto give a white suspension
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-548c361f10cd42d48350dcddbbbcefee
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008483B2

Reaction notes

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