Diisopropylethylamine → HCID 178478400, compound

HRID 2044827Notes

Reaction equation

HRID 2044827 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][NH2:20])=[CH:7]2.[Cl:21][C:22]1[N:30]=[C:29]2[C:25]([NH:26][CH:27]=[N:28]2)=[C:24](Cl)[N:23]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:21][C:22]1[N:30]=[C:29]2[C:25]([N:26]=[CH:27][NH:28]2)=[C:24]([NH:20][CH2:19][C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[N:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53244122,6-DichloropurineHCID 59264634(8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

Product 1

HCID 178478400HCID 178478400, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine (0.100 g, 0.33 mmol), 2,6-dichloropurine (0.062 g, 0.33 mmol, 1 eq) and DIEA (0.07 mL, 0.4 mmol, 1.2 eq) in ethanol (5 mL). 2-Chloro-N-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=615 nM] was obtained after purification as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.44 (1 H, s), 8.15 (1 H, s), 8.04 (1 H, dd, J=8.5, 1.2 Hz), 7.96 (1 H, d, J=6.7 Hz), 7.60 (1 H, d, J=7.3 Hz), 7.61 (1 H, t, J=7.9 Hz), 7.54 (1 H, d, J=6.7 Hz), 7.50 (1 H, t, J=6.7 Hz), 7.44 (1 H, t, J=7.3 Hz), 4.62 (2 H, d, J=26.9 Hz) Mass Spectrum (ESI) m/e=455.0 and 457.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cdc698edeab8480db4c02be98145ef37
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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