Trifluoroacetohydrazide → HCID 86683635, compound

HRID 1509247Notes

Reaction equation

HRID 1509247 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=S)[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:36][C:37]([F:43])([F:42])[C:38]([NH:40][NH2:41])=O>CC1C=CC(C)=CC=1>[C:29]1([C:19]2[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:8]4([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][CH2:10][CH2:9]4)=[CH:13][CH:14]=3)=[N:28][C:22]3[O:23][CH2:24][C:25]4[N:26]([C:38]([C:37]([F:43])([F:42])[F:36])=[N:40][N:41]=4)[C:21]=3[CH:20]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 229753TrifluoroacetohydrazideHCID 86683631Tert-butyl (1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

Product 1

HCID 86683635HCID 86683635, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of tert-butyl(1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (70 mg, 0.144 mmol) and 2,2,2-trifluoroacetohydrazide (7.3 mg, 0.057 mmol) in p-xylene (1 ml) was heated to 150° C. for 30 minutes under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure and purified by Biotage silica gel chromatography (gradient 0% to 20% ethyl acetate in n-hexanes) to give the title compound (7 mg, 20%). LCMS (Method D): RT=1.633 min, M+1=564. 1H NMR (500 MHz, CDCl3): 7.96 (1H, s), 7.36-7.27 (7H, m), 7.21-7.17 (2H, m), 5.63 (2H, s), 2.55-2.40 (4H, m), 2.14-1.98 (1H, m), 1.88-1.78 (1H, m), 1.37-1.20 (9H, bs).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated to dryness under reduced pressure
  3. custompurified by Biotage silica gel chromatography (gradient 0% to 20% ethyl acetate in n-hexanes)

Sources & evidence

ORD record
ord-88cff949a84e4bf6bc38caed24dcbde5
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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