Diisopropylethylamine → N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

HRID 888163Notes

Reaction equation

HRID 888163 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:21])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3F)=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][C:31]([CH2:32][NH2:33])=[C:26]2[CH:25]=[N:24]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([C:14]3[C:15]([NH:33][CH2:32][C:31]4[CH:30]=[CH:29][N:28]=[C:27]5[NH:23][N:24]=[CH:25][C:26]=45)=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:21])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 55285368(1H-Pyrazolo[3,4-b]pyridin-4-yl)methanamine2×HCID 68908856N-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-fluoro-nicotinamide

Product 1

HCID 58942003N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

N-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-fluoro-nicotinamide (60 mg, 0.201 mmol) was dissolved in NMP (0.5 mL), then C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (36 mg, 0.243 mmol) and DIEA (70 μL, 0.401 mmol) were added. The mixture was heated at 120° C. overnight. Additional C-(1H-pyrazolo[3,4-b]pyridin-4-yl)-methylamine (14 mg, 0.094 mmol) and DIEA (35 μL, 0.200 mmol) were added and the mixture was heated at 120° C. overnight. The mixture was partitioned between water and EtOAc. The mixture was diluted with EtOAc then washed with water and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification was achieved by preparative TLC (10% MeOH/CH2Cl2) to give N-(4,4-dimethyl-1,2,3,4-tetrahydro-7-quinolinyl)-2-((1H-pyrazolo[3,4-b]pyridin-4-ylmethyl)amino)-3-pyridinecarboxamide as a yellow solid. MS m/e 428.2(M+H)+. Calc'd for C24H25N7O—427.51.

Workup

  1. temperaturethe mixture was heated at 120° C. overnight
  2. customThe mixture was partitioned between water and EtOAc
  3. additionThe mixture was diluted with EtOAc
  4. washthen washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-73d103710e0941d49e1b3b84b416b9e1
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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