Diisopropylethylamine → N-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 216751Notes

Reaction equation

HRID 216751 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:27]=[C:26]([O:28][CH3:29])[NH:25][C:24]2=[N:30][CH:31]=[CH:32][C:23]=12.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[C:23]3[CH:32]=[CH:31][NH:30][C:24]=3[N:25]=[C:26]([O:28][CH3:29])[N:27]=1)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59264634(8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamineHCID 178494204HCID 178494204, compound

Product 1

HCID 25070973N-((8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methyl)-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-4-amine

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), 4-chloro-2-methoxy-pyrrolo[2,3-d]pyrimidine (0.061 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)-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-4-amine [PI3Kδ IC50=5420 nM] was obtained after purification as a tan solid. 1H NMR (400 MHz, DMSO-d) δ ppm 11.28 (1 H, s), 8.37 (1H, s), 8.03 (1H, dd, J=8.4, 1.0 Hz), 7.94-7.99 (1H, m), 7.94 (1H, dd, J=7.6, 1.4 Hz), 7.40-7.65 (5H, m), 6.88 (1H, dd, J=3.3, 2.2 Hz), 6.47 (1H, s), 4.59 (2H, s), 3.67 (3H, s) Mass Spectrum (ESI) m/e=450.1 and 452.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5bba0642eff447368f893270619b5bee
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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