Diisopropylethylamine → HCID 118390028, compound

HRID 1477974Notes

Reaction equation

HRID 1477974 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[C:5]([CH3:25])=[CH:4][N:3]=1.[CH3:26][N:27]1[CH:31]=[C:30]([NH2:32])[CH:29]=[N:28]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:25][C:5]1[C:6]([NH:8][CH:9]2[C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)=[N:7][C:2]([NH:32][C:30]2[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 118390067HCID 118390067, compound

Product 1

HCID 118390028HCID 118390028, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl 4-((2-chloro-5-methylpyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (0.35 g, 0.95 mmol) and 1-methyl-1H-pyrazol-4-amine (0.14 g, 1.43 mmol) in n-BuOH (5 mL) was added DIPEA (0.25 g, 1.9 mmol). The reaction mixture was stirred at 150° C. for 16 h then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the product as black oil (0.45 g, 86%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-78f0e4c3a72e4fb996d394aace6e2b0d
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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