Diisopropylethylamine → HCID 178505654, compound

HRID 1397697Notes

Reaction equation

HRID 1397697 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]=[C:14]([F:18])[CH:13]=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]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=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 57708000HCID 57708000, compound

Product 1

HCID 178505654HCID 178505654, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-(3-fluorophenyl)quinolin-3-yl)methanamine (0.030 g, 0.11 mmol), 6-Chloropurine (0.019 g, 0.13 mmol, 1.2 eq) and DIEA in n-butanol (3 mL). N-((8-chloro-2-(3-fluorophenyl)quinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=74 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.41 (s, 1 H), 8.13 (s, 1 H), 7.88-8.02 (m, 4 H), 7.59 (dd, J=4.40, 2.20 Hz, 4 H), 4.80-4.98 (m, 2 H), Mass Spectrum (ESI) m/e=405 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b1434d72d08b4ecf99bec22d3ff0a668
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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