Diisopropylethylamine → HCID 89726084, compound

HRID 592044Notes

Reaction equation

HRID 592044 reaction equation
[NH2:1][C:2]12[C:8]([CH3:10])([CH3:9])[C:5]([CH3:11])([CH2:6][CH2:7]1)[C:4](=[O:12])[CH2:3]2.Cl[C:14]1[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([NH2:21])[C:15]=1[N+:22]([O-:24])=[O:23].CCN(C(C)C)C(C)C>CC(O)C>[NH2:21][C:16]1[C:15]([N+:22]([O-:24])=[O:23])=[C:14]([NH:1][C:2]23[C:8]([CH3:9])([CH3:10])[C:5]([CH3:11])([CH2:6][CH2:7]2)[C:4](=[O:12])[CH2:3]3)[C:19]([Cl:20])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 216001904-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-oneHCID 468676602-Amino-4,5-dichloro-3-nitropyridine

Product 1

HCID 89726084HCID 89726084, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

4-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (8) (1.1 g, 5.29 mmol)) and 4,5-dichloro-3-nitropyridin-2-amine (1 g, 4.81 mmol) were taken in IPA (30 ml) and DIPEA (4.6 ml, 26.44 mmol)) was added to the reaction mixture which was then heated at 60° C. for 24 h when TLC confirmed completion of reaction. The reaction mixture was cooled to rt and concentrated in vacuuo. Pure product (9) (1.63 g, 92%) was obtained as a yellow solid after purification by column chromatography using silica gel (100-200 mesh). NMR: δ (1H, 400 MHz, CDCl3): 0.87 (3H, s), 0.97 (3H, s), 1.05 (3H, s), 1.44-1.54 (1H, m), 1.70-1.80 (1H, m), 1.90-2.20 (1H, m), 2.30-2.40 (1H, m), 2.47 (1H, dd, J=3.2, 18.0 Hz), 2.88 (1H, d, J=18.4 Hz), 6.55 (2H, s), 7.85 (1H, s), 7.96 (1H, s) LCMS: (254 nm): [M+H]+ 339.10 (86.27%)

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction mixture was cooled to rt
  3. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-e96b5159e65d4d7693adb7f7724d901e
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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