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

HRID 1056634Notes

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]([Cl: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>[Cl:24][C:5]1[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)=[N:7][C:2]([NH:37][C:31]2[CH:32]=[CH:33][C:34]3[C:29]([CH:30]=2)=[N:28][N:27]([CH3:26])[C:35]=3[CH3:36])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (621.8 mg, 1.666 mmol) and 2,3-dimethylindazol-6-amine hydrochloride (999.6 mg, 5.057 mmol) in n-BuOH (6 mL) was added DIPEA (1.10 g, 8.43 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 (EtOAc/PE (v/v)=2/1) to give the title compound as a pale brown solid (452.1 mg, 54.5%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1)

Sources & evidence

ORD record: ord-07d0c3663e564f2faabb73a8bdb087d8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399637B2

Reaction notes

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