Diisopropylethylamine → HCID 178463553, compound

HRID 1192580Notes

Reaction equation

HRID 1192580 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:23]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[C:16]([F:30])[CH:15]=1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[F:30][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:23]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368531(3R)-1-[7-(1-aminoethyl)-5-fluoroquinolin-8-yl]pyrrolidin-3-olHCID 178419477HCID 178419477, compound

Product 1

HCID 178463553HCID 178463553, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (14.5 mg, 0.0727 mmol), (3R)-1-[7-(1-aminoethyl)-5-fluoroquinolin-8-yl]pyrrolidin-3-ol (10 mg, 0.04 mmol), and N,N-diisopropylethylamine (0.013 mL, 0.073 mmol) in isopropyl alcohol (0.1 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resulting mixture was purified on a RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the desired product. First peak retention time 1.32 minutes, LCMS calculated for C20H21FN7O (M+H)+: m/z=394.2; Found: 394.2. Second peak retention time 1.40 minutes, LCMS calculated for C20H21FN7O (M+H)+: m/z=394.2; Found: 394.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resulting mixture was purified on a RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-0d87317c92544bc796a18c74acd8bd75
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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