2-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazine → Ethyl {2-methyl-4-[(propyl{6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl}amino)methyl]phenoxy}acetate

HRID 1269658Notes

Reaction equation

HRID 1269658 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:3]=1.[CH3:18][C:19]1[CH:31]=[C:30]([CH2:32][NH:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:28][C:20]=1[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(N(CC1C=CC(OCC(OCC)=O)=C(C)C=1)C1C=NC=C(C2C=CC(Cl)=CC=2)N=1)CCC>>[CH3:18][C:19]1[CH:31]=[C:30]([CH2:32][N:33]([CH2:34][CH2:35][CH3:36])[C:2]2[CH:7]=[N:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[N:3]=2)[CH:29]=[CH:28][C:20]=1[O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 3

HCID 184483272-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazineHCID 58622861Ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetateHCID 58622900Ethyl [4-({butyl[6-(4-chlorophenyl)pyrazin-2-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 58622880Ethyl {2-methyl-4-[(propyl{6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl}amino)methyl]phenoxy}acetateYield 11.5%

Procedure

Using 2-chloro-6-(4-(trifluoromethyl)phenyl]pyrazine (0.303 g, 1 mmol) and ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate (0.4 g, 1.5 mmol) and the synthetic procedure described for Intermediate 77. Purification by Biotage™ chromatography (Si, 40 g) eluting 9:1–7:3 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (56 mg).

Workup

  1. customPurification by Biotage™ chromatography (Si, 40 g)
  2. washeluting 9:1–7:3 cyclohexane

Sources & evidence

ORD record
ord-4fbd4ce35a264a6daf82427457347848
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

Loading…