Diisopropylethylamine → HCID 178458649, compound

HRID 1437439

Reaction equation

HRID 1437439 reaction equation
[Cl:1][C:2]1[C:3]([NH:12][C:13]2[CH:17]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[NH:15][N:14]=2)=[N:4][C:5](Cl)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[C:3]([NH:12][C:13]2[CH:17]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[NH:15][N:14]=2)=[N:4][C:5]([NH:31][C@H:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH3:30])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 178458612HCID 178458612, compound

Product 1

HCID 178458649HCID 178458649, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 3,6-dichloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyridin-2-amine (Method 59, 0.25 g, 0.75 mmol), (S)-1-(4-fluoro-phenyl)-ethylamine (0.13 g, 0.90 mmol) and DIEA (0.16 ml, 0.94 mmol) in n-BuOH (3 ml) was heated in a sealed tube at 145° C. for 2 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane-EtOAc=1:1) to give the title compound as a yellow solid (0.32 g, 98%). 1H NMR (400 MHz) δ 12.22 & 11.40 (s, 1H), 9.74 & 9.37 (s, 1H), 8.93 (d, J=7.6 Hz, 1H), 8.33 & 8.27 (s, 1H), 7.34 & 7.27 (m, 2H), 7.12 & 7.05 (m, 2H), 5.75 & 5.62 (s, 1H), 5.35 & 5.25 (m, 1H), 4.66 & 4.03 (m, 1H), 1.55 (d, J=6.4 Hz, 3H), 1.29 (d, J=6.0 Hz, 6H). MS: Calcd.: 434. Found: [M+H]+ 435.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (hexane-EtOAc=1:1)

Sources & evidence

ORD record
ord-8588a15f39234379884e9d144c93c547
Source dataset
uspto-grants-2009_11
Patent number
US07622482B2

Linked notes

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