Water → HCID 57812838, compound

HRID 2274423Notes

Reaction equation

C(=O)(O)[O-].[Na+].[CH3:6][N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[F:14][C:15]1[C:21](F)=[CH:20][C:18]([NH2:19])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.O>CN(C=O)C>[F:14][C:15]1[C:21]([N:10]2[CH2:11][CH2:12][CH2:13][N:7]([CH3:6])[CH2:8][CH2:9]2)=[CH:20][C:18]([NH2:19])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

36.2 g of sodium bicarbonate and 29.5 g of N-methyl-homopiperazine are added to a solution of 15 g of 4,5-difluoro-2-nitroaniline in 120 mL of anhydrous DMF. The reaction medium is heated at 80° C. using an oil bath for 2H30. The reaction medium is cooled to ambient temperature, and then poured into 400 mL of water. The mixture is cooled using an ice bath and stirred, and precipitation occurs. The precipitate is filtered off through sintered glass. The yellow solid is rinsed with water. The solid is dried in an oven at 40° C. 21 g of 4-fluoro-5-(4-methylperhydro-1,4-diazepin-1-yl)-2-nitrophenylamine are obtained in the form of a yellow solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.90 (m, 2H); 2.27 (s, 3H); 2.50 (m masked, 2H); 2.64 (m, 2H); 3.46 (m, 2H); 3.52 (m, 2H); 6.21 (d, J=9.0 Hz, 1H); 7.24 (broad s, 2H); 7.59 (d, J=16.0 Hz, 1H). EI mass spectrum: m/z=268: M+. (base peak)—m/z=253: (M−CH3)+—m/z=198: (M−C4H8N)+—m/z=70: C4H8N+—m/z=57: C3H7N+.

Workup

temperatureThe reaction medium is cooled to ambient temperature
temperatureThe mixture is cooled
customprecipitation
filtrationThe precipitate is filtered off through sintered glass
washThe yellow solid is rinsed with water
customThe solid is dried in an oven at 40° C

Sources & evidence

ORD record: ord-42f4b160b258497eb9baa720c0b27149
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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