Sodium hydride → HCID 57556191, compound

HRID 2074503Notes

Reaction equation

HRID 2074503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.[H-].[Na+].[I:23][C:24]1[C:32]2[C:27](=[N:28][CH:29]=[N:30][C:31]=2N)[NH:26][N:25]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][N:19]2[C:31]3=[N:30][CH:29]=[N:28][C:27]([NH2:26])=[C:32]3[C:24]([I:23])=[N:25]2)=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67090634HCID 67090634, compoundHCID 178508725HCID 178508725, compound

Product 1

HCID 57556191HCID 57556191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to Procedure I using (2-(2-fluorophenyl)-8-methylquinolin-3-yl)methanamine (0.200 g, 0.7 mmol), NaH (0.031 g, 60% in oil, 0.77 mmol, 1.1 eq) and 3-iodo-1H-pyrazolo{3,4-d}pyrimidin-4-amine (0.201 g, 0.77 mmol, 1.1 eq) in DMF. 1-((2-(2-fluorophenyl)-8-methylquinolin-3-yl)methyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine [PI3Kδ IC50=4 nM] was obtained after purification as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.09 (1 H, s), 8.00 (1 H, s), 7.96 (1 H, s), 7.80 (1 H, d, J=7.9 Hz), 7.63 (1 H, d, J=7.3 Hz), 7.46-7.53 (1 H, m), 7.30 (1 H, dt), 7.08 (1 H, dd, J=7.6, 1.5 Hz), 7.02 (1 H, d, J=7.9 Hz), 6.91 (1 H, t, J=7.3 Hz), 5.46-5.54 (2 H, m), 2.90 (3 H, s) Mass Spectrum (ESI) m/e=511.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1b63664694fb4641be120741cbdd6c41
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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