2,4-Difluoronitrobenzene → HCID 178457839, compound

HRID 518742Notes

Reaction equation

HRID 518742 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.F[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[N+:32]([O-:34])=[O:33]>C(#N)C>[F:31][C:29]1[CH:28]=[CH:27][C:26]([N+:32]([O-:34])=[O:33])=[C:25]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[CH:30]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 178457872HCID 178457872, compound

Product 1

HCID 178457839HCID 178457839, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (0.1 g, 0.453 mmol) and DIPEA (0.237 mL, 1.359 mmol) in ACN (3 mL) was added 2,4-difluoro-1-nitrobenzene (0.072 g, 0.453 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated, adsorbed onto a plug of silica gel, and purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide cis-4-(5-fluoro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide as a yellow powder (0.123 g, 84% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography
  3. washeluting with 0-100% EtOAc in DCM

Sources & evidence

ORD record
ord-85e6b540204e46be81af4921c7b70674
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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