Diisopropylethylamine → HCID 24965143, compound

HRID 1666429Notes

Reaction equation

HRID 1666429 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[CH3:26][C:27]1[N:32]=[CH:31][C:30]([NH:33][C:34](=O)[O:35]C2C=CC=CC=2)=[CH:29][CH:28]=1.NC1C=NC(C)=CC=1.C(N(C(C)C)CC)(C)C>C(#N)C>[F:25][C:3]([F:2])([F:24])[C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:34]([NH:33][C:30]3[CH:31]=[N:32][C:27]([CH3:26])=[CH:28][CH:29]=3)=[O:35])[CH2:15][CH2:14]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2433135-Amino-2-methylpyridineHCID 54438385Phenyl 6-methylpyridin-3-ylcarbamateHCID 668757324-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride

Product 1

HCID 24965143HCID 24965143, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride (200 mg, 0.541 mmol, from Example 53, Step 5) and phenyl 6-methylpyridin-3-ylcarbamate (123 mg, 0.541 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-amino-6-methylpyridine) and diisopropylethylamine (0.20 mL, 1.15 mmol) were combined in acetonitrile (5 mL) and stirred at room temperature. After 16 h, the reaction was concentrated and the residue was purified by silica gel chromatography (50-100% EtOAc:CH2Cl2) to afford the title compound (220 mg) as a white solid. MS APCI M+ 468.2, 375.2, 334.1 M− 466.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.41-2.45 (m, 2H) 2.46 (s, 3H) 2.54 (td, J=5.90, 1.26 Hz, 2H) 3.50-3.55 (m, 2H) 3.58-3.65 (m, 2H) 6.43 (s, 1H) 6.91-6.96 (m, 2H) 7.06-7.12 (m, 3H) 7.20 (d, J=8.52 Hz, 1H) 7.35-7.42 (m, 1H) 7.59-7.68 (m, 2H) 7.77 (dd, J=8.45, 2.62 Hz, 1H) 8.43 (d, J=2.78 Hz, 1H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by silica gel chromatography (50-100% EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-809ff8653dff4ef39d363cec21a3173b
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

Loading…