Diisopropylethylamine → N-((8-chloro-2-phenoxyquinolin-3-yl)methyl)-9H-purin-6-amine

HRID 2044861Notes

Reaction equation

HRID 2044861 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([CH2:19][NH2:20])=[CH:7]2.Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([CH2:19][NH:20][C:22]1[N:30]=[CH:29][N:28]=[C:27]3[C:23]=1[N:24]=[CH:25][NH:26]3)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57708028HCID 57708028, compound

Product 1

HCID 178477944N-((8-chloro-2-phenoxyquinolin-3-yl)methyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-phenoxyquinolin-3-yl)-methanamine (0.110 g, 0.360 mmol), 6-chloropurine (0.072 g, 0.46 mmol, 1.2 eq) and DIEA (0.72 mmol, 2.0 eq) in n-butanol (3 mL). N-((8-chloro-2-phenoxyquinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=125 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.18-8.24 (s, 1 H), 8.14-8.20 (s, 1 H), 7.85-7.91 (d, J=7.58, 1 H), 7.72-7.79 (d, J=7.34, 1 H), 7.47-7.55 (m, 3 H), 7.42-7.47 (m, 3 H), 7.35-7.42 (m, 1 H), 4.01-4.14 (m, 2 H), Mass Spectrum (ESI) m/e=403 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0677ba2556944f7c9b1cacb3efd1f081
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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