Diisopropylethylamine → HCID 118390011, compound

HRID 1478005Notes

Reaction equation

HRID 1478005 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:26])[CH:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]3)[CH2:10]2)[C:5]([Cl:27])=[CH:4][N:3]=1.Cl.[CH3:29][N:30]1[CH:34]=[C:33]([NH2:35])[CH:32]=[N:31]1.CCN(C(C)C)C(C)C>CCCCO>[Cl:27][C:5]1[C:6]([N:8]([CH3:26])[CH:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:14]3)[CH2:10]2)=[N:7][C:2]([NH:35][C:33]2[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390097HCID 118390097, compound

Product 1

HCID 118390011HCID 118390011, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of tert-butyl 2-((2,5-dichloropyrimidin-4-yl)(methyl)amino)-7-azaspiro[4.5]decane-7-carboxylate (470 mg, 1.13 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (235.7 mg, 1.76 mmol) in n-BuOH (5 mL) was added DIPEA (482.6 g, 3.74 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 white solid (280 mg, 52.0%).

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-9eaef6ec0d71470fa4c6dd76020b32c7
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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