Diisopropylethylamine → HCID 24968343, compound

HRID 1666344Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C:10](=O)[O:11]C1C=CC=CC=1)=[O:8].Cl.[NH:20]1[CH2:25][CH2:24][C:23](=[CH:26][C:27]2[CH:28]=[C:29]([CH:41]=[CH:42][CH:43]=2)[O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][N:32]=2)[CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C>C(#N)C>[F:39][C:37]([F:40])([F:38])[C:34]1[CH:35]=[CH:36][C:31]([O:30][C:29]2[CH:28]=[C:27]([CH:43]=[CH:42][CH:41]=2)[CH:26]=[C:23]2[CH2:24][CH2:25][N:20]([C:10]([NH:9][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:8])=[O:11])[CH2:21][CH2:22]2)=[N:32][CH:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Phenyl picolinoylcarbamate (145 mg, 0.599 mmol, from Step 1), 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 to form a residue. The residue was purified by silica gel chromatography (20-75% EtOAc in CH2Cl2) to provide the title compound (0.152 g). MS APCI M+ 483.1, 376.1, 335.1; M− 481.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.45-2.72 (m, 4H) 3.64 (m, 4H) 6.47 (s, 1H) 6.96-7.06 (m, 2H) 7.08-7.20 (m, 2H) 7.40 (td, J=7.65, 0.91 Hz, 1H) 7.63 (ddd, J=7.63, 4.76, 1.23 Hz, 1H) 8.02 (td, J=7.75, 1.69 Hz, 1H) 8.08 (ddd, J=8.71, 2.55, 0.61 Hz, 1H) 8.18 (dt, J=7.86, 1.08 Hz, 1H) 8.42 (td, J=1.72, 0.80 Hz, 1H) 8.67 (ddd, J=4.76, 1.69, 0.95 Hz, 1H).

Workup

temperatureAfter 3 hours the mixture was cooled to room temperature
concentrationconcentrated
customto form a residue
customThe residue was purified by silica gel chromatography (20-75% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-25f7b23d63544c87a5d3c74263e2ea62
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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