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Triethylamine → HCID 67204782, compound

HRID 1626321
Notes
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Reaction equation

HRID 1626321 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.Cl.[CH3:25][C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=1[N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][CH2:41][NH2:42])[CH2:35][CH2:34]1.C(N(CC)CC)C>C(O)C>[CH3:25][C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=1[N:33]1[CH2:34][CH2:35][N:36]([CH2:39][CH2:40][CH2:41][NH:42][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:6]3[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:37][CH2:38]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70664367HCID 70664367, compoundHCID 86046565HCID 86046565, compound

Product 1

HCID 67204782HCID 67204782, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-chloro-8,9-diphenyl-9H-purine (150 mg, 0.49 mmol) and 3-(4-(2,3-dimethylphenyl)piperazin-1-yl)propan-1-amine dihydrochloride (313 mg, 0.98 mmol) in ethanol (4.9 mL) was added triethyl amine (0.27 mL, 1.96 mmol) and stirred at 80° C. for 15 hrs. The resulting reaction mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer thus separated was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was purified by preparative HPLC (purification system, Gilson) to provide the title compound (117 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water
  5. customThe organic layer thus separated
  6. dry with materialwas dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product thus obtained
  10. customwas purified by preparative HPLC (purification system, Gilson)

Sources & evidence

ORD record
ord-a7a025d91abc4fa69d2e2c0937649b25
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785453B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes