Hydrochloric Acid → HCID 178427929, compound

HRID 510896Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[N:11][N:12](C(OCC)C)[CH:13]=2)[C:5]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[C:4]([CH:27]([NH2:29])[CH3:28])[CH:3]=1.Br[C:31]1[N:39]=[CH:38][N:37]=[C:36]2[C:32]=1[N:33]=[CH:34][NH:35]2.C(N(CC)C(C)C)(C)C.Cl.O>C(O)C.O1CCCC1.CO>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:13]=[N:12][NH:11][CH:10]=2)[C:5]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[C:4]([CH:27]([NH:29][C:31]2[N:39]=[CH:38][N:37]=[C:36]3[C:32]=2[N:33]=[CH:34][NH:35]3)[CH3:28])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-{4-chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3′,5′-difluoro-5-methylbiphenyl-2-yl}ethanamine (0.074 g, 0.18 mmol), 6-bromo-9H-purine (0.053 g, 0.26 mmol) and N,N-diisopropylethylamine (0.061 mL, 0.35 mmol) in ethanol (0.6 mL) was heated at 100° C. overnight. The residue was concentrated and treated with 1.0 M hydrogen chloride in water (1.0 mL, 1.0 mmol) in tetrahydrofuran (1 mL) overnight. The mixture was diluted with MeOH and purified on prep LCMS (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min) to afford the desired product. LCMS calculated for C23H19ClF2N7 (M+H)+: m/z=466.1. found: 466.1.

Workup

concentrationThe residue was concentrated
custompurified on prep LCMS (XBridge C18 Column
washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record: ord-50cf76ee1c1b4c42a388810237d7043f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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