Triethylamine → HCID 19810584, compound

HRID 2352435Notes

Reaction equation

HRID 2352435 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[NH2:11][CH2:12][CH:13]([OH:36])[CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH:21]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.C(N(CC)CC)C>CO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH:21]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH:13]([OH:36])[CH2:12][NH:11][C:7]34[N:6]=[CH:5][N:4]=[C:3]3[CH:2]=[N:10][CH:9]=[N:8]4)[CH2:16][CH2:17]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53592776-ChloropurineHCID 10406287HCID 10406287, compound

Product 1

HCID 19810584HCID 19810584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-chloropurine (0.728 g, 4.7 mmol), 1-amino-3-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]-2-propanol (1.73 g, 4.77 mmol) and triethylamine (1.36 mL, 9.5 mmol) in MeOH (20 mL) was heated to reflux for 7 days and the solvent was removed in vacuo. The residue was dissolved in CHCl3 and the extracted with aqueous sodium bicarbonate (2×100 mL); the organic phase was dried over sodium sulfate and evaporated to give a solid which was purified by flash chromatography on silica gel with 5% MeOH in CHCl3. The product was a colorless solid which was triturated with ether, 1.5 g (70%), mp 140°-170° C.; IR (KBr) 3000 cm-1 ; 300 MHz 1H NMR (CDCl3); δ: 8.17 (s, 1H), 8.11 (s, 1H), 7.5-7.0 (m, 8H), 4.90 (br s, 1H), 4.34 (s, 1H), 3.87 (br s, 1H), 3.7-2.0 (m, 12H); MS 480 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 days
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in CHCl3
  5. extractionthe extracted with aqueous sodium bicarbonate (2×100 mL)
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. customevaporated
  8. customto give a solid which
  9. customwas purified by flash chromatography on silica gel with 5% MeOH in CHCl3
  10. customwas triturated with ether, 1.5 g (70%), mp 140°-170° C.

Sources & evidence

ORD record
ord-bf5a8a294e674269bef00fc86bc5b5b7
Source dataset
uspto-grants-1989_10
Patent number
US04876257

Reaction notes

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