Diisopropylethylamine → HCID 178463548, compound

HRID 1192713Notes

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:20]=[C:19]([CH:21]([NH2:23])[CH3:22])[C:18]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)=[C:17]2[C:13]=1[CH:14]=[N:15][N:16]2[CH3:32].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:11][C:12]1[CH:20]=[C:19]([CH:21]([NH:23][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:22])[C:18]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)=[C:17]2[C:13]=1[CH:14]=[N:15][N:16]2[CH3:32]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-bromo-9H-purine (0.30 g, 1.5 mmol), 1-[4-chloro-7-(3,5-difluorophenyl)-1-methyl-1H-indazol-6-yl]ethanamine (0.439 g, 1.36 mmol), and N,N-diisopropylethylamine (0.48 mL, 2.7 mmol) in isopropyl alcohol (5 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 C21H17ClF2N7 (M+H)+: m/z=440.1; Found: 440.1. 1H NMR (DMSO-d6, 400 MHz) δ 8.29 (1H, br s), 8.10 (1H, s), 8.05 (1H, s), 8.04 (1H, s), 7.62 (1H, s), 7.52 (1H, d, J=8.8 Hz), 7.43 (1H, m), 7.31 (1H, d, J=8.8 Hz), 5.10(1H, br s), 3.41 (3H, s), 3.35 (1H, m), 1.41 (3H, d, J=6.8 Hz) ppm. 19F NMR (DMSO-d6, 376 MHz) δ −110 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-996bb98f10254ba7a6bd3a83e4557c61
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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