Diisopropylethylamine → 2-[2-[1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

HRID 451425Notes

Reaction equation

HRID 451425 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)[S:6][N:5]=1.Cl[C:17]1[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[N:18]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][CH:12]([NH:15][C:17]3[N:22]=[C:21]([C:23]([OH:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=4)[N:18]=3)[CH2:13][CH2:14]2)[S:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 673442811-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine dihydrochlorideHCID 866336402-[2-Chloro-6-(4-trifluoromethyl-phenyl)pyrimidine-4-yl]-propan-2-ol

Product 1

HCID 533534272-[2-[1-(3-Methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamine dihydrochloride (54.2 mg, 0.2 mmol), 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol (69.7 mg, 0.22 mmol) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in dioxane (2 mL) was heated at 200° C. in a microwave oven for 2 hours. The reaction was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 (v/v) as eluent. The title compound was obtained as a brown viscous oil (26 mg, 27%). MS ISP (m/e): 479.1 (100) [(M+H)+].

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 (v/v) as eluent

Sources & evidence

ORD record
ord-0a56ce7895e546008992c2cdfca4bdff
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…