Diisopropylethylamine → tert-butyl 8-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylate

HRID 1056626Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:26])[CH:9]2[CH2:25][CH2:24][C:12]3([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.Cl.[CH3:28][N:29]1[C:37]([CH3:38])=[C:36]2[C:31]([CH:32]=[C:33]([NH2:39])[CH:34]=[CH:35]2)=[N:30]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:28][N:29]1[C:37]([CH3:38])=[C:36]2[C:31]([CH:32]=[C:33]([NH:39][C:2]3[N:7]=[C:6]([N:8]([CH3:26])[CH:9]4[CH2:10][CH2:11][C:12]5([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13]5)[CH2:24][CH2:25]4)[CH:5]=[CH:4][N:3]=3)[CH:34]=[CH:35]2)=[N:30]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 8-((2-chloropyrimidin-4-yl)(methyl)amino)-2-azaspiro[4.5]decane-2-carboxylate (500.0 mg, 1.3 mmol) and 2,3-dimethyl-2H-indazol-6-amine hydrochloride (778.6 mg, 3.9 mmol) in n-BuOH (10 mL) was added DIPEA (1.04 g, 8.0 mmol). The reaction mixture was stirred at 150° C. in a sealed tube overnight, then cooled down to rt, and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the title compound as a yellow solid (657 mg, 100%).

Workup

temperaturecooled down to rt
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10)

Sources & evidence

ORD record: ord-74eae05867714b42845e5c6c9c8c2481
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399637B2

Reaction notes

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