Diisopropylethylamine → HCID 178478022, compound

HRID 2044826Notes

Reaction equation

HRID 2044826 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]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH2:20])=[CH:7]2.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)C>[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]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH:20][C:22]1[N:30]=[CH:29][N:28]=[C:27]3[C:23]=1[N:24]=[CH:25][NH:26]3)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 59264634(8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

Product 1

HCID 178478022HCID 178478022, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine (0.100 g, 0.33 mmol), 6-chloropurine (0.051 g, 0.33 mmol, 1 eq) and DIEA (0.07 mL, 0.4 mmol, 1.2 eq) in ethanol (3 mL). N-((8-chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=68 nM] was obtained after purification as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.37 (1 H, s), 8.11 (1 H, s), 8.08 (1 H, s), 8.00 (1 H, dd, J=8.2, 1.2 Hz), 7.93 (1 H, dd, J=7.4, 1.2 Hz), 7.42-7.67 (5 H, m) Mass Spectrum (ESI) m/e=421.0 and 423.1 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-284466272e6b48178c908cfb4c4e006e
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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