3-Chloro-5-cyclopropylbenzoic acid → 3-Chloro-5-cyclopropyl-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-benzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:10]=1)[C:5]([OH:7])=O.FC1C=C(C=C(C(F)(F)F)C=1)[C:18]([N:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[O:35][CH3:36])C)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:10]=1)[C:5]([N:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[O:35][CH3:36])[CH3:18])=[O:7]Participants
Procedure
The title compound was prepared in analogy to example 90, from 3-chloro-5-cyclopropylbenzoic acid and 4-(4-fluoro-2-methoxyphenyl)-N-methylpyridin-3-amine (0.18 g, 775 μmol, example 129, intermediate) after a reaction time of 41 hours at room temperature. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless solid (0.012 g; 3%). MS (ESI): m/z=411.13 [M+H]+.
Workup
- customThe compound was purified by silica gel chromatography on a 10 g column
- washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
- customThe product was purified by preparative HPLC (Gemini NX column)
- customThe product was purified by preparative HPLC (Gemini NX column)
Sources & evidence
- ORD record
- ord-80b06ecc55d24c73a898ca9e8bb980a1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987307B2
Reaction notes
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