Diisopropylethylamine → HCID 178423774, compound

HRID 2044842Notes

Reaction equation

HRID 2044842 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH2:22][NH2:23])=[CH:7]2.CCN(C(C)C)C(C)C.Cl[C:34]1[N:42]=[CH:41][N:40]=[C:39]2[C:35]=1[NH:36][CH:37]=[N:38]2>CCO>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:19])[F:20])[C:8]([CH2:22][NH:23][C:34]1[N:42]=[CH:41][N:40]=[C:39]3[C:35]=1[N:36]=[CH:37][NH:38]3)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707817(8-Methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine

Product 1

HCID 178423774HCID 178423774, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to Procedure H using (8-methyl-2-(2-(trifluoromethyl)-phenyl)quinolin-3-yl)methanamine (0.1 g, 0.316 mmol, 1 eq) in EtOH (2 mL) was treated with iPr2NEt (0.07 mL, 0.4 mmol, 1.2 eq) followed by 6-chloropurine (0.049 g, 0.317 mmol, 1 eq). After purification, N-((8-methyl-2-(2-(trifluoro-methyl)phenyl)quinolin-3-yl)methyl)-9H-purin-6-amine as yellow syrup. The yellow syrup was triturated with CH2Cl2 and filtered to provide N-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=91 nM] as yellow syrup. 1H NMR (DMSO-d6) δ ppm 12.93 (1 H, s), 7.98-8.31 (4 H, m), 7.90 (1 H, d, J=7.8 Hz), 7.74-7.82 (2 H, m), 7.69 (2 H, t, J=6.5 Hz), 7.59 (1 H, d, J=7.0 Hz), 7.42-7.52 (1 H, m), 4.42-4.77 (2 H, m), 2.62 (3 H, s). Mass Spectrum (ESI) m/e=435.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification, N-((8-methyl-2-(2-(trifluoro-methyl)phenyl)quinolin-3-yl)methyl)-9H-purin-6-amine as yellow syrup
  3. customThe yellow syrup was triturated with CH2Cl2
  4. filtrationfiltered

Sources & evidence

ORD record
ord-586d8d9a645b4f7bbdd13aa47641d63d
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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