Diisopropylethylamine → HCID 178463550, compound

HRID 510832Notes

Reaction equation

HRID 510832 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[CH:15]=[C:16]([Cl:32])[C:17]([CH2:29][C:30]#[N:31])=[C:18]([C:27]#[N:28])[C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:32][C:16]1[C:17]([CH2:29][C:30]#[N:31])=[C:18]([C:27]#[N:28])[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[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:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 866667666-(1-Aminoethyl)-4-chloro-3-(cyanomethyl)-3'-fluorobiphenyl-2-carbonitrileHCID 178419477HCID 178419477, compound

Product 1

HCID 178463550HCID 178463550, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-9H-purine (22 mg, 0.11 mmol), 6-(1-aminoethyl)-4-chloro-3-(cyanomethyl)-3′-fluorobiphenyl-2-carbonitrile (17 mg, 0.054 mmol), and N,N-diisopropylethylamine (0.032 mL, 0.18 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 (8 mg, 30%). LCMS calculated for C22H16ClFN7 (M+H)+: m/z=432.1. found: 432.1.

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-26d30d8e438a452ca3e934f550839939
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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