Diisopropylethylamine → tert-butyl 5-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1056646Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][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]([CH3:24])=[CH:4][N:3]=1.Cl.[CH3:26][N:27]1[C:35]([CH3:36])=[C:34]2[C:29]([CH:30]=[C:31]([NH2:37])[CH:32]=[CH:33]2)=[N:28]1.CCN(C(C)C)C(C)C>CCCCO>[CH3:26][N:27]1[C:35]([CH3:36])=[C:34]2[C:29]([CH:30]=[C:31]([NH:37][C:2]3[N:7]=[C:6]([NH:8][CH:9]4[CH2:10][CH:11]5[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:13][CH:12]5[CH2:23]4)[C:5]([CH3:24])=[CH:4][N:3]=3)[CH:32]=[CH:33]2)=[N:28]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 5-((2-chloro-5-methylpyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (421.5 mg, 1.19 mmol) and 2,3-dimethylindazol-6-amine hydrochloride (734.5 mg, 3.72 mmol) in n-BuOH (10 mL) was added DIPEA (795.2 mg, 6.09 mmol). The reaction mixture was stirred at 150° C. under microwave for 2 h 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 brown oil (570.5 mg, 100%).

Workup

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

Sources & evidence

ORD record: ord-a64513e3d7f94365b6cda8243519e4b2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399637B2

Reaction notes

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