Diisopropylethylamine → HCID 178505451, compound

HRID 1397703Notes

Reaction equation

HRID 1397703 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][CH:12]=[C:13]([F:20])[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][CH:12]=[C:13]([F:20])[CH:14]=2)[N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707967HCID 57707967, compound

Product 1

HCID 178505451HCID 178505451, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (2-(2-chlorophenyl)-6-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)-6-fluoroquinolin-3-yl)methyl)-9H-purin-6-amine [PI3Kδ IC50=1683 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.44 (s, 1 H), 8.14 (s, 1 H), 8.07-8.11 (m, 2 H), 7.66-7.71 (m, 1 H), 7.59-7.66 (m, 1 H), 7.49-7.55 (m, 2 H), 7.40-7.46 (m, 1 H), 7.34-7.40 (m, 1 H), 4.05-4.17 (m, 2 H), Mass Spectrum (ESI) m/e=405 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-189f4b0875b740fd96a970d31aaea4b0
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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