Diisopropylethylamine → Ethyl 3-(5-(2-(((2-chloro-2'-methyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405261Notes

Reaction equation

Br[CH2:2][C:3]1[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:23])=[N:20][CH:21]=1.[Cl:32][C:33]1[CH:38]=[C:37]([NH2:39])[CH:36]=[CH:35][C:34]=1[C:40]1[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][C:41]=1[CH3:50].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:32][C:33]1[CH:38]=[C:37]([NH:39][CH2:2][C:3]2[C:8]([CH:9]([CH3:11])[CH3:10])=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:4]=2[C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:23])=[N:20][CH:21]=2)[CH:36]=[CH:35][C:34]=1[C:40]1[CH:45]=[CH:44][C:43]([C:46]([F:47])([F:48])[F:49])=[CH:42][C:41]=1[CH3:50]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 3-(5-(2-(bromomethyl)-3-isopropyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (27 mg, 0.05 mmol), 2-chloro-2′-methyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-amine (20 mg, 0.07 mmol) and iPr2NEt (27 μL, 0.16 mmol) were dissolved in toluene (3 mL) and the resulting mixture was heated at 100° C. After 16 h the resulting mixture was concentrated and purified via column chromatography to yield the title compound.

Workup

concentrationAfter 16 h the resulting mixture was concentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-a2266bc6d0054eafa3f43085332922b6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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