Diisopropylethylamine → HCID 178463533, compound

HRID 1192546Notes

Reaction equation

HRID 1192546 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:23]=[C:22]([Cl:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[N:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1)[CH3:13].C(N(CC)C(C)C)(C)C>C(O)C>[Cl:24][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([N:25]2[CH2:26][CH2:27][CH:28]([OH:31])[CH2:29][CH2:30]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:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58368669HCID 58368669, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178463533HCID 178463533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.096 g, 0.48 mmol), 1-[2-(1-aminoethyl)-4-chloro-1-naphthyl]piperidin-4-ol (0.074 g, 0.24 mmol), and N,N-diisopropylethylamine (0.084 mL, 0.48 mmol) in ethanol (0.8 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resulting residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated to dryness. The resulting residue 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 as the free base. LCMS calculated for C22H24ClN6O (M+H)+: m/z=423.2; Found: 423.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. additionthe resulting residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. customevaporated to dryness
  9. customThe resulting residue was purified on a RP-HPLC (XBridge C18 column
  10. 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-e458e60ef6f04327817f3f5f40512a7c
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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