Diisopropylethylamine → HCID 178461894, compound

HRID 216799Notes

Reaction equation

HRID 216799 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:18]([NH2:20])[CH3:19])[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9]2)=[CH:4][CH:3]=1.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>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:18]([NH:20][C:22]3[N:30]=[CH:29][N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][NH:26]4)[CH3:19])[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707848HCID 57707848, compound

Product 1

HCID 178461894HCID 178461894, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (1S)-1-(7-fluoro-2-(pyridin-3-yl)-quinolin-3-yl)ethanamine (0.067 g, 0.236 mmol), 6-chloropurine (0.044 g, 0.283 mmol, 1.2 eq) and DIEA (0.48 mmol, 2.0 eq) in n-butanol (3 mL). N-((S)-1-(7-fluoro-2-(pyridin-3-yl)quinolin-3-yl)ethyl)-9H-purin-6-amine [PI3Kδ IC50=23 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.99 (s, 1H), 8.57-8.65 (m, 2H), 8.33 (d, J=7.83 Hz, 1H), 8.16 (s, 1H), 8.08 (s, 1H), 7.85-7.96 (m, 2H), 1.62 (d, 3H), Mass Spectrum (ESI) m/e=402 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1f348fef209548e097a5a6b9d3e1d00c
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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