Diisopropylethylamine → HCID 178461888, compound

HRID 216798Notes

Reaction equation

HRID 216798 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[N:13]=[CH:14][S:15][CH:16]=1)[C:8]([C@@H:17]([NH2:19])[CH3:18])=[CH:7]2.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[NH:23][CH:24]=[N:25]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[N:13]=[CH:14][S:15][CH:16]=1)[C:8]([C@@H:17]([NH:19][C:21]1[N:29]=[CH:28][N:27]=[C:26]3[C:22]=1[N:23]=[CH:24][NH:25]3)[CH3:18])=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707900HCID 57707900, compound

Product 1

HCID 178461888HCID 178461888, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (1S)-1-(8-chloro-2-(thiazol-4-yl)-quinolin-3-yl)ethanamine (0.045 g, 0.155 mmol), 6-chloropurine (0.029 g, 0.19 mmol, 1.2 eq) and DIEA (0.33 mmol, 2.0 eq) in n-butanol (3 mL). N-((S)-1-(8-chloro-2-(thiazol-4-yl)quinolin-3-yl)ethyl)-9H-purin-6-amine [PI3Kδ IC50=16 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 9.22 (s, 1H), 8.63 (s, 1H), 8.44-8.46 (m, 1H), 8.42 (s, 1H), 8.34 (s, 1H), 7.88-7.93 (m, 2H), 7.56 (t, 1H), 1.77 (d, 3H), Mass Spectrum (ESI) m/e=408 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0f58c656b621468e9fa3075a433afe19
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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