Water → HCID 67025457, compound

HRID 217272

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([NH2:20])=[C:18](Br)[C:17]([Cl:22])=[C:16]([C:23]([F:26])([F:25])[F:24])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([NH2:20])=[CH:18][C:17]([Cl:22])=[C:16]([C:23]([F:24])([F:25])[F:26])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of the compound obtained in Step B (0.2 g), tris(trimethylsilyl)-silane (0.16 ml), and 2,2′-azobis(2-methylpropionitrile) (10 mg) in toluene (10 ml) was stirred at 85° C. for 2 hours under a nitrogen atmosphere. More tris(trimethylsilyl)silane (0.3 ml) and more 2,2′-azobis(2-methylpropionitrile) (5 mg) were then added and the reaction mixture was heated to 85° C. for 16 hours. The reaction mixture was cooled to ambient temperature, poured into water, extracted with ethyl acetate, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 1:1) afforded 3-amino-5-chloro-6-trifluoromethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.160 g) as a solid. MS (ES+) 324/326 (M-isoprene); 1H NMR (400 MHz, CDCl3) 1.48 (s, 9H), 1.84 (m, 4H), 2.78 (m, 1H), 2.88 (m, 2H), 4.25 (m, 2H), 4.42 (s, 2H), 7.46 (s, 1H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9fbe68e98dfb40c395ffb8d6e2a87586
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193362B2

Linked notes

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