Diisopropylethylamine → HCID 178463539, compound

HRID 1192595Notes

Reaction equation

Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH2:24])[CH3:23])[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:11][C:12]1[CH:21]=[C:20]([CH:22]([NH:24][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:23])[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-bromo-9H-purine (74 mg, 0.37 mmol), 1-[5-chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanamine (0.075 g, 0.25 mmol), and N,N-diisopropylethylamine (0.087 mL, 0.50 mmol) in isopropyl alcohol (2 mL) was heated at 90° C., under nitrogen, overnight. The mixture was evaporated and the resulting mixture was purified on a RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the desired product. LCMS calculated for C22H17ClFN6 (M+H)+: m/z=419.1; Found: 419.1. 1H NMR (DMSO-d6, 400 MHz) δ 8.58 (2H, m), 8.30 (2H, m), 8.06 (1H, s), 8.00 (1H, d, J=5.2 Hz), 7.92 (1H, d, J=6.0 Hz), 7.58 (2H, m), 7.37˜7.20 (2H, m), 5.19 (1H, m), 3.29 (1H, br s), 1.39 (3H, m) ppm. 19F NMR (DMSO-d6, 376 MHz) δ −113.5 ppm.

Workup

customThe mixture was evaporated
customthe resulting mixture was purified on a RP-HPLC (XBridge C18 column
washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)

Sources & evidence

ORD record: ord-d1406ef4e6cd4f6f9c59a7cb2ad7479d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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