N-methyl-2-pyrrolidone → 6-(4-(3-(4-hydroxy-4-methylpiperidin-1-yl)propoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-d]pyridine-4-carbonitrile

HRID 517990Notes

Reaction equation

HRID 517990 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2C=[C:18]([C:26]#[N:27])[C:19]3[N:23]=[N:22][N:21]([CH3:24])[C:20]=3[CH:25]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29])(=O)=O.Cl.[CH3:33][C:34]1([OH:40])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C[N:42]1C(=O)CCC1>>[OH:40][C:34]1([CH3:33])[CH2:39][CH2:38][N:37]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:25]=[C:20]4[N:21]([CH3:24])[N:22]=[N:23][C:19]4=[C:18]([C:26]#[N:27])[N:42]=3)=[CH:12][C:11]=2[C:28]([F:29])([F:30])[F:31])[CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 219492954-Methylpiperidin-4-ol hydrochlorideHCID 866733533-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate

Product 1

HCID 533303936-(4-(3-(4-hydroxy-4-methylpiperidin-1-yl)propoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-d]pyridine-4-carbonitrile

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-(4-cyano-1-methyl-1H-benzo[d][1,2,3]triazol-6-yl)-2-(trifluoromethyl)phenoxy)propyl methanesulfonate (100 mg) and 4-methylpiperidin-4-ol hydrochloride (166 mg) in NMP (2 ml) was heated at 100° C. under microwave conditions for 30 minutes. The mixture was purified by HPLC to give the expected product (9.4 mg). 1H NMR (CD3OD) δ: 8.55 (s, 1H), 8.35-8.42 (m, 2H), 7.32 (d, 1H), 4.44 (s, 3H), 4.25 (t, 2H), 2.76-2.89 (m, 4H), 2.63-2.75 (m, 2H), 2.13 (quin, 2H), 1.64-1.80 (m, 4H), 1.24 (s, 3H). MS m/z 475 (M+H).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-b364fc6e328d4fa3b2a83d20ac2df108
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

Loading…