Diisopropylethylamine → HCID 178505917, compound

HRID 216788Notes

Reaction equation

HRID 216788 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]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)[C:8]([CH2:20][NH2:21])=[CH:7]2.Cl[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[NH:25][CH:26]=[N:27]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:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[CH:17]=1)[C:8]([CH2:20][NH:21][C:23]1[N:31]=[CH:30][N:29]=[C:28]3[C:24]=1[N:25]=[CH:26][NH:27]3)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707803HCID 57707803, compound

Product 1

HCID 178505917HCID 178505917, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-(3,5-difluorophenyl)-quinolin-3-yl)methanamine (0.105 g, 0.345 mmol), 6-chloropurine (0.064 g, 0.41 mmol, 1.2 eq) and DIEA (0.70 mmol, 2.0 eq) in n-butanol (3 mL). N-((8-chloro-2-(3,5-difluorophenyl)quinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=76 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.48 (s, 1H), 8.35 (s, 1H), 8.24 (s, 1H), 7.86-7.94 (m, 2H), 7.52-7.61 (m, 1H), 7.27-7.35 (m, 2H), 6.96-7.06 (m, 1H), 4.73 (d, J=5.71, 2H), Mass Spectrum (ESI) m/e=423 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-84f4f897b28446bd8998fbdec4d3d110
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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