Diisopropylethylamine → HCID 118390113, compound

HRID 1477993Notes

Reaction equation

HRID 1477993 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)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:26][N:27]1[CH:31]=[C:30]([NH2:32])[CH:29]=[N:28]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:26][N:27]1[CH:31]=[C:30]([NH:32][C:2]2[N:7]=[C:6]([NH:8][CH:9]3[C:13]4([CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:12][N:11]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:10]3)[CH:5]=[CH:4][N:3]=2)[CH:29]=[N:28]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 173542681-methyl-1H-pyrazol-4-amineHCID 118390001HCID 118390001, compound

Product 1

HCID 118390113HCID 118390113, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl 4-((2-chloropyrimidin-4-yl)amino)-2-azaspiro[4.4]nonane-2-carboxylate (528 mg, 1.50 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (240.52 mg, 1.8 mmol) in n-BuOH (8 mL) was added DIPEA (581.60 mg, 4.5 mmol). After addition, the reaction mixture was stirred at 150° C. overnight. The resulting mixture was concentrated in vacuo and purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1 to 20/1) to give the product as a yellow oil (550 mg, 88.9%).

Workup

  1. additionAfter addition
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. custompurified by silica gel column chromatography (DCM/MeOH (v/v)=50/1 to 20/1)

Sources & evidence

ORD record
ord-8c29fe3482824460b19ccdd5f12d6a87
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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