3-Fluoro-5-(trifluoromethyl)benzoyl chloride → HCID 86613811, compound

HRID 2378133Notes

Reaction equation

HRID 2378133 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:9][C@@H:8]1[CH3:35])=[O:6])([CH3:3])[CH3:2].[F:36][C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:40](Cl)=[O:41]>N1C=CC=CC=1>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([N:19]([CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C:40](=[O:41])[C:39]2[CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=[C:37]([F:36])[CH:38]=2)[CH2:9][C@@H:8]1[CH3:35])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 86613809HCID 86613809, compound

Product 1

HCID 86613811HCID 86613811, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepare the title compound by essentially following the procedure described for the synthesis of Example 47, using (+/−)-cis-4-(3,5-bis-trifluoromethyl-benzylamino)-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.210 g, 0.415 mmol), 3-fluoro-5-trifluoromethyl benzoyl chloride (0.095 mL, 0.631 mmol) and pyridine (0.10 mL). Purify using silica gel column chromatography (gradient eluent, 0-30% ethyl acetate in hexane) to provide the title compound (0.246 g, 88%). MS (ES+): 696 (M+H).

Workup

  1. customdescribed for the synthesis of Example 47
  2. customPurify

Sources & evidence

ORD record
ord-016c8d565a264a06913e53eb2eca80f0
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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