Diisopropylethylamine → HCID 178505394, compound

HRID 1397704Notes

Reaction equation

HRID 1397704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([F:20])[CH:14]=2)[N:9]=1.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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH2:18][NH:19][C:23]2[N:31]=[CH:30][N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][NH:27]3)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:21])=[C:13]([F:20])[CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707811HCID 57707811, compound

Product 1

HCID 178505394HCID 178505394, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (2-(2-chlorophenyl)-6,7-difluoro-quinolin-3-yl)methanamine (0.080 g, 0.279 mmol), 6-chloropurine (0.065 g, 0.42 mmol, 1.5 eq) and DIEA (0.56 mmol, 2.0 eq) in n-butanol (3 mL). N-((2-(2-chlorophenyl)-6,7-difluoroquinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=551 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.46 (s, 1 H), 8.13 (s, 1 H), 8.09 (s, 1 H), 7.83-7.94 (m, 3 H), 7.49-7.55 (m, 2 H), 7.41-7.48 (m, 1 H), 7.35-7.41 (m, 1 H), 4.89-4.85 (m, 2H), Mass Spectrum (ESI) m/e=423 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-de9f6cf02fba4361965cb647d823c90b
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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