Diisopropylethylamine → HCID 178505892, compound

HRID 1397705Notes

Reaction equation

HRID 1397705 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[C:25]([CH2:26][NH2:27])=[CH:24][C:23]2[C:18](=[C:19]([Cl:28])[CH:20]=[CH:21][CH:22]=2)[N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:30]1[N:38]=[CH:37][N:36]=[C:35]2[C:31]=1[NH:32][CH:33]=[N:34]2.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[C:16]1[C:25]([CH2:26][NH:27][C:30]2[N:38]=[CH:37][N:36]=[C:35]3[C:31]=2[N:32]=[CH:33][NH:34]3)=[CH:24][C:23]2[C:18](=[C:19]([Cl:28])[CH:20]=[CH:21][CH:22]=2)[N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707788HCID 57707788, compound

Product 1

HCID 178505892HCID 178505892, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (2-(2-(benzyloxy)-5-fluorophenyl)-8-chloroquinolin-3-yl)methanamine (0.021 g, 0.053 mmol), 6-chloropurine (0.012 g, 0.06 mmol, 1.5 eq) and DIEA (0.1 mmol, 2.0 eq) in n-butanol (3 mL). N-((2-(2-(benzyloxy)-5-fluorophenyl)-8-chloroquinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=31 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.38 (s, 1 H), 8.12 (s, 1 H), 8.07 (s, 1 H), 7.90 (s, 1 H), 7.88 (s, 1 H), 7.52-7.59 (t, 1 H), 7.21-7.25 (m, 2 H), 7.19 (m, 4 H), 7.06-7.12 (m, 2 H), 5.05-5.10 (m, 2H), 4.90-4.96 (s, 2H), Mass Spectrum (ESI) m/e=511 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-197940fa343141188bba53a70162f749
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

Loading…