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 537199Notes

Reaction equation

HRID 537199 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.[C:9]([N:13]1[CH:21]=[C:20]2[C:15]([C:16](=[O:40])[NH:17][C:18]3([CH2:26][CH2:25][N:24]([C:27]([C:29]4[CH:38]=[C:37]5[C:32]([CH:33]=[CH:34][C:35](Cl)=[N:36]5)=[CH:31][CH:30]=4)=[O:28])[CH2:23][CH2:22]3)[CH2:19]2)=[N:14]1)([CH3:12])([CH3:11])[CH3:10]>>[C:9]([N:13]1[CH:21]=[C:20]2[C:15]([C:16](=[O:40])[NH:17][C:18]3([CH2:26][CH2:25][N:24]([C:27]([C:29]4[CH:38]=[C:37]5[C:32]([CH:33]=[CH:34][C:35]([N:2]([CH3:3])[CH3:1])=[N:36]5)=[CH:31][CH:30]=4)=[O:28])[CH2:23][CH2:22]3)[CH2:19]2)=[N:14]1)([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 732927272'-tert-butyl-1-(2-chloroquinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

Product 1

HCID 674917052'-tert-butyl-1-(2-(dimethylamino)quinoline-7-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-oneYield 25%

Conditions

Temperature
70 °C

Procedure

A solution of dimethylamine in tetrahydrofuran (2.2 mL, 4.4 mmol, 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

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. customPurification by reversed-phase HPLC

Sources & evidence

ORD record
ord-028e939321e84dd984a22b1319067728
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

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