Dimethylamine → 2'-tert-butyl-1-(2-(dimethylamino)quinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

HRID 881015Notes

Reaction equation

[CH3:1][NH:2][CH3:3].[C:4]([N:8]1[CH:16]=[C:15]2[C:10]([C:11](=[O:35])[NH:12][C:13]3([CH2:21][CH2:20][N:19]([C:22]([C:24]4[CH:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30](Cl)=[N:31]5)=[CH:26][CH:25]=4)=[O:23])[CH2:18][CH2:17]3)[CH2:14]2)=[N:9]1)([CH3:7])([CH3:6])[CH3:5]>O1CCCC1>[C:4]([N:8]1[CH:16]=[C:15]2[C:10]([C:11](=[O:35])[NH:12][C:13]3([CH2:21][CH2:20][N:19]([C:22]([C:24]4[CH:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30]([N:2]([CH3:3])[CH3:1])=[N:31]5)=[CH:26][CH:25]=4)=[O:23])[CH2:18][CH2:17]3)[CH2:14]2)=[N:9]1)([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of dimethylamine in tetrahydrofuran (2.2 mL, 4.4 mmmol, 2.0 M) was added to 2′-tert-butyl-1-(2-chloroquinoline-7-carbonyl)-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(2′H)-one (100 mg, 0.2 mmol). The reaction vessel was sealed and the mixture was heated to 70° C. for 15 hours. The reaction was cooled to room temperature and concentrated. Purification by reversed-phase HPLC gave the title compound (25 mg, 25%). +ESI (M+H) 461.2; HPLC retention time 1.96 minutes (Method A).

Workup

customThe reaction vessel was sealed
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customPurification by reversed-phase HPLC

Sources & evidence

ORD record: ord-fc1b195a7318429798e69e977346a323
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993586B2

Reaction notes

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