2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178515981, compound

HRID 706116Notes

Reaction equation

HRID 706116 reaction equation
CS[C:3]1[NH:4][CH:5]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14](=[O:17])[NH:13][CH:12]=2)[C:7](=[O:9])[N:8]=1.[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=2)=[CH:21][C:20]=1[C:35]([F:38])([F:37])[F:36]>N1C=CC=CC=1>[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][C:3]3[NH:4][CH:5]=[C:6]([CH2:10][C:11]4[CH:16]=[CH:15][C:14](=[O:17])[NH:13][CH:12]=4)[C:7](=[O:9])[N:8]=3)=[CH:26][CH:25]=2)=[CH:21][C:20]=1[C:35]([F:36])([F:37])[F:38]

Participants

4

Reactant 2

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamineHCID 178503538HCID 178503538, compound

Product 1

HCID 178515981HCID 178515981, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-methylsulfanyl-5-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-1H-pyrimidin-4-one (20 mg, 0.08 mmol, 1 eq) and 2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (40 mg, 0.127 mmol, 1.58 eq) were heated in 300 μl of dry pyridine at 150° C. for 16 hours. Solvent was then evaporated and the resulting crude was purified by chromatography on BIOTAGE SP1 purification device using 10 g normal phase silica SNAP column and DCM/30% MEOH in DCM solvent system (gradient 5-100% of 30% MeOH in DCM in 25 column volumes). Solvent from the gathered fractions of appropriate composition was evaporated and obtained was 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-1H-pyrimidin-4-one (5.4 mg, yield=11.7%, purity=90%). MS: [M+H]=517.34. 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.81 (t, J=7.032 Hz, 2H), 3.23 (s, 2H), 3.43-3.53 (m, 2H), 6.24 (d, J=9.45 Hz, 1H), 6.36 (br.s., 1H), 7.03-7.14 (m, 3H), 7.20-7.37 (m, 4H), 7.41 (d, J=2.55 Hz, 1H), 7.54 (s, 1H), 7.70 (d, J=8.82 Hz, 1H).

Workup

  1. customSolvent was then evaporated
  2. customthe resulting crude was purified by chromatography on BIOTAGE SP1 purification device
  3. customSolvent from the gathered fractions of appropriate composition was evaporated
  4. customobtained

Sources & evidence

ORD record
ord-bb358ccd8d7043d5a8c1b5b0d3e5812f
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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