Diisopropylethylamine → HCID 178492196, compound

HRID 510862Notes

Reaction equation

HRID 510862 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:28][CH3:29])=[C:16]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[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]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[C:15]([O:28][CH3:29])=[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 86666792HCID 86666792, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178492196HCID 178492196, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-9H-purine (8.5 mg, 0.043 mmol), 1-[3-(1-aminoethyl)-5-chloro-2-methoxy-6-methylphenyl]pyrrolidin-2-one (11 mg, 0.039 mmol), and N,N-diisopropylethylamine (0.014 mL, 0.078 mmol) in isopropyl alcohol (0.1 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 C19H22ClN6O2 (M+H)+: m/z=401.1. found: 401.1.

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-5c552dec0f274cf09fc1f09c51c53c79
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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