Diisopropylethylamine → HCID 178492184, compound

HRID 510878Notes

Reaction equation

HRID 510878 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.[NH2:11][CH:12]([C:14]1[C:15]([O:32][CH3:33])=[C:16]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]([NH2:31])=[O:30])[CH:23]=2)[C:17]([CH3:21])=[C:18]([Cl:20])[CH:19]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:20][C:18]1[C:17]([CH3:21])=[C:16]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]([NH2:31])=[O:30])[CH:23]=2)[C:15]([O:32][CH3:33])=[C:14]([CH:12]([NH:11][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[CH3:13])[CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86666800HCID 86666800, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178492184HCID 178492184, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-9H-purine (23 mg, 0.12 mmol), 3′-(1-aminoethyl)-5′-chloro-4-fluoro-2′-methoxy-6′-methylbiphenyl-3-carboxamide (36 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.037 mL, 0.21 mmol) in isopropyl alcohol (0.4 mL) was heated at 90° C. under nitrogen overnight. The mixture was evaporated and the resulting mixture was purified on RP-HPLC (XBridge C18 Column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. LCMS calculated for C22H21ClFN6O2 (M+H)+: m/z=455.1. found: 455.1.

Workup

  1. customThe mixture was evaporated
  2. customthe resulting mixture was purified on RP-HPLC (XBridge C18 Column
  3. 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-b2aef3c255354886b586768375c72d0d
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…