3,5-Bis(trifluoromethyl)benzyl bromide → HCID 86613812, compound

HRID 2378135Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([NH:21][C:22](=[O:24])[CH3:23])[CH2:9][C@@H:8]1[CH3:25])=[O:6])([CH3:3])[CH3:2].[F:26][C:27]([F:41])([F:40])[C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:31]Br.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[C@H:10]([N:21]([C:22](=[O:24])[CH3:23])[CH2:31][C:30]2[CH:33]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:35]=[C:28]([C:27]([F:26])([F:40])[F:41])[CH:29]=2)[CH2:9][C@@H:8]1[CH3:25])=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 1225733,5-Bis(trifluoromethyl)benzyl bromide

HCID 2733832Lithium Hexamethyldisilazide

HCID 68902103HCID 68902103, compound

Product 1

HCID 86613812HCID 86613812, compoundYield 30%

Procedure

Prepare the title compound by essentially following the procedure described in Example 49, Step 2, by replacing (+/−)-N-(1-cyclopently-6-methoxy-2-methyl-1,2,3,4-tetrahydro-[1,5]napthyridin-4-yl)-acetamide with cis-4-acetylamino-2-methyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.065 g, 0.018 mmol), and using 3,5-bis trifluoromethyl benzylbromide and lithium hexamethyldisilazide. Purify using silica gel column chromatography (gradient eluent, neat ethyl acetate) to afford the title compound (0.031 g, 30%). MS (ES+): 586 (M+H).

Workup

customPurify

Sources & evidence

ORD record: ord-f2bba037753c44b8b7c86d81b3a17b5c
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470705B2

Reaction notes

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