Sodium hydride → 1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 2074495Notes

Reaction equation

HRID 2074495 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19]Cl)=[CH:7]2.[H-].[Na+].[I:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[N:30][C:31]=2[NH2:33])[NH:26][N:25]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][N:26]1[C:27]3=[N:28][CH:29]=[N:30][C:31]([NH2:33])=[C:32]3[C:24]([I:23])=[N:25]1)=[CH:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 592646338-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinolineHCID 178508725HCID 178508725, compound

Product 1

HCID 575561871-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure I using 8-chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline (0.235 g, 0.73 mmol), NaH (0.047 g 60% in oil, 1.17 mmol, 1.6 eq) and 3-iodo-1H-pyrazolo{3,4-d}pyrimidin-4-amine (0.209 g, 0.8 mmol, 1.1 eq) in DMF. 1-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained after purification as a white solid [PI3KδIC50=14 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (1 H, s), 8.09 (1 H, dd, J=8.6, 1.2 Hz), 7.98-8.05 (2 H, m), 7.66 (1 H, t), 7.48 (1 H, dd, J=8.2, 0.8 Hz), 7.36 (1 H, dt, J=7.8, 1.6 Hz), 7.25 (1 H, dt, J=7.4, 1.2 Hz), 7.13 (1 H, dd, J=7.4, 1.6 Hz), 5.53 (2 H, s) Mass Spectrum (ESI) m/e=547.0 and 549.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cb90352598664b9990b1b9db8c1fe7ae
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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