Diisopropylethylamine → HCID 178474183, compound

HRID 510847Notes

Reaction equation

HRID 510847 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:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:18]([NH:27][C:28](=[O:30])[CH3:29])[C:17]([CH3:31])=[C:16]([Cl:32])[CH:15]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:32][C:16]1[CH:15]=[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])[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:18]([NH:27][C:28](=[O:30])[CH3:29])[C:17]=1[CH3:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86666776HCID 86666776, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178474183HCID 178474183, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-9H-purine (22 mg, 0.11 mmol), N-[6-(1-aminoethyl)-4-chloro-3′-fluoro-3-methylbiphenyl-2-yl]acetamide (32 mg, 0.10 mmol), and N,N-diisopropylethylamine (0.035 mL, 0.20 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 C22H21ClFN6O (M+H)+: m/z=439.1. found: 439.3.

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-cbf3aa9ac5104972b08c4bac19d3af88
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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