Diisopropylethylamine → HCID 118390065, compound

HRID 1478013Notes

Reaction equation

HRID 1478013 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:17][CH2:16][CH:15]3[CH:11]([CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[CH2:10]2)[C:5]([Cl:25])=[CH:4][N:3]=1.Cl.[CH3:27][N:28]1[CH:32]=[C:31]([NH2:33])[CH:30]=[N:29]1.C(N(C(C)C)C(C)C)C>CCCCO>[Cl:25][C:5]1[C:6]([NH:8][CH:9]2[CH2:17][CH2:16][CH:15]3[CH:11]([CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[CH2:10]2)=[N:7][C:2]([NH:33][C:31]2[CH:30]=[N:29][N:28]([CH3:27])[CH:32]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390102HCID 118390102, compound

Product 1

HCID 118390065HCID 118390065, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydro-1H-isoindole-2(3H)-carboxylate (767.3 mg, 1.98 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (411.5 mg, 3.08 mmol) in n-BuOH (5 mL) was added N-ethyldiisopropylamine (792.9 g, 6.14 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography ((EtOAc/PE (v/v)=1/1) to give the title compound as a pale yellow solid (493 mg, 55.6%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography ((EtOAc/PE (v/v)=1/1)

Sources & evidence

ORD record
ord-10e676aee7474d24aa939a65abb0538a
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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