Diisopropylethylamine → HCID 118390039, compound

HRID 1478089Notes

Reaction equation

HRID 1478089 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:24])[CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]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.CCN(C(C)C)C(C)C>CCCCO>[Cl:25][C:5]1[C:6]([N:8]([CH3:24])[CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:15][CH:11]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 118390009HCID 118390009, compound

Product 1

HCID 118390039HCID 118390039, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)(methyl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (249.1 mg, 0.64 mmol) and 1-methylpyrazol-4-amine hydrochloride (333.1 mg, 2.49 mmol) in n-BuOH (10 mL) was added DIPEA (452.0 mg, 3.46 mmol). The reaction mixture was stirred at 150° C. in a sealed tube for 28 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1) to give the title compound as brown oil (230.8 mg, 80.1%).

Workup

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

Sources & evidence

ORD record
ord-3d4d0a4f82ed4e29a056a3155bfdb9eb
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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