Diisopropylethylamine → HCID 24968684, compound

HRID 1666345Notes

Reaction equation

HRID 1666345 reaction equation
CC1([C:8](NC(=O)OC2C=CC=CC=2)=[O:9])C=CC=CN1.[CH3:20][C:21]1[N:26]=[C:25]([C:27]([NH2:29])=[O:28])[CH:24]=[CH:23][CH:22]=1.Cl.[NH:31]1[CH2:36][CH2:35][C:34](=[CH:37][C:38]2[CH:39]=[C:40]([CH:52]=[CH:53][CH:54]=2)[O:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][N:43]=2)[CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:20][C:21]1[N:26]=[C:25]([C:27]([NH:29][C:8]([N:31]2[CH2:36][CH2:35][C:34](=[CH:37][C:38]3[CH:54]=[CH:53][CH:52]=[C:40]([O:41][C:42]4[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:49])[F:50])=[CH:44][N:43]=4)[CH:39]=3)[CH2:33][CH2:32]2)=[O:9])=[O:28])[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 123629366-Methylpyridine-2-carboxamideHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochlorideHCID 86623893HCID 86623893, compound

Product 1

HCID 24968684HCID 24968684, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Phenyl 2-methylpicolinoylcarbamate (150 mg, 0.585 mmol, prepared according to the procedure in Example 15, Step 1 from 6-methyl-pyridine-2-carboxamide), 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (175 mg, 0.472 mmol) (from Example 1, Step 5), and diisopropylethyl amine (0.16 mL, 0.92 mmol) were combined in acetonitrile (5 mL) and warmed to 50° C. After 3 hours the mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (10-75% EtOAc in CH2Cl2) to provide the title compound (0.197 g). MS APCI M+ 497.2, 376.12, 335.12; 1H NMR (400 MHz, CD3OD) δ ppm 2.61 (s, 3H) 2.46-2.70 (m, 4H) 3.64 (m, 4H) 6.47 (s, 1H) 6.96-7.06 (m, 2H) 7.08-7.19 (m, 2H) 7.40 (td, J=7.69, 0.73 Hz, 1H) 7.50 (dd, J=7.80, 0.46 Hz, 1H) 7.88 (t, J=7.71 Hz, 1H) 7.98 (ddd, J=7.74, 0.99, 0.50 Hz, 1H) 8.08 (ddd, J=8.73, 2.48, 0.66 Hz, 1H) 8.42 (td, J=1.75, 0.87 Hz, 1H).

Workup

  1. temperatureAfter 3 hours the mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (10-75% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-53953b3836fe44b99313791cfd8730c8
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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