Diisopropylethylamine → HCID 178505444, compound

HRID 1397702Notes

Reaction equation

HRID 1397702 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:20])=[CH:13][CH:14]=2)[N:9]=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>[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:22]2[N:30]=[CH:29][N:28]=[C:27]3[C:23]=2[N:24]=[CH:25][NH:26]3)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([F:20])=[CH:13][CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707966HCID 57707966, compound

Product 1

HCID 178505444HCID 178505444, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (2-(2-chlorophenyl)-7-fluoroquinolin-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)-7-fluoroquinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=225 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.49 (s, 1 H), 8.14 (s, 1 H), 8.03-8.10 (m, 2 H), 7.66-7.73 (m, 2 H), 7.47-7.56 (m, 2 H), 7.43-7.44 (m, 1 H), 7.33-7.40 (m, 1 H), 4.10-4.18 (m, 2 H), Mass Spectrum (ESI) m/e=405 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-363b0f1853f04fbf9f37ee61b9965cde
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

Loading…