Water → HCID 57812840, compound

HRID 2274432Notes

Reaction equation

C(=O)(O)[O-].[K+].[F:6][C:7]1[C:13](F)=[CH:12][C:10]([NH2:11])=[C:9]([N+:15]([O-:17])=[O:16])[CH:8]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].O>CN(C=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:13]2[CH:12]=[C:10]([NH2:11])[C:9]([N+:15]([O-:17])=[O:16])=[CH:8][C:7]=2[F:6])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

2.4 g of potassium bicarbonate and 1 g of 4,5-difluoro-2-nitroaniline are added to a solution of 3.3 g of piperazine-1-carboxylic acid tert-butyl ester in 30 mL of anhydrous DMF. The reaction medium is heated at 60° C. using an oil bath for 30 minutes. The reaction medium is cooled to ambient temperature, then 150 mL of water are added thereto, and precipitation occurs. The precipitate is filtered off through sintered glass. The solid is dried in an oven at 50° C. 1.4 g of 4-(5-amino-2-fluoro-4-nitrophenyl)piperazine-1-carboxylic acid tert-butyl ester are obtained in the form of a yellow solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.42 (s, 9H); 3.14 (m, 4H); 3.46 (m, 4H); 6.43 (d, J=8.0 Hz, 1H); 7.36 (broad s, 2H); 7.66 (d, J=14.5 Hz, 1H). EI mass spectrum: m/z=340 M+., m/z=284 (M−C4H+., m/z=264 (m/z=284−HF)+, m/z=57 C4H+ (base peak).

Workup

customfor 30 minutes
temperatureThe reaction medium is cooled to ambient temperature
customprecipitation
filtrationThe precipitate is filtered off through sintered glass
customThe solid is dried in an oven at 50° C

Sources & evidence

ORD record: ord-7b2f78915a80468da142a9bbb9ea60cd
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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