Triethylamine → HCID 10293403, compound

HRID 1767450Notes

Reaction equation

HRID 1767450 reaction equation
C([O:4][CH:5]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6]1)(=O)C.[CH2:12]([N:19]1[C:27]2[C:26](=[O:28])[N:25]([CH3:29])[C:24](=[O:30])[N:23]([CH3:31])[C:22]=2[N:21]=[C:20]1Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>CC(O)C>[CH2:12]([N:19]1[C:27]2[C:26](=[O:28])[N:25]([CH3:29])[C:24](=[O:30])[N:23]([CH3:31])[C:22]=2[N:21]=[C:20]1[N:7]1[CH2:6][CH:5]([OH:4])[CH2:11][NH:10][CH2:9][CH2:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3253727-Benzyl-8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dioneHCID 14999084HCID 14999084, compound

Product 1

HCID 10293403HCID 10293403, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

[1,4]Diazepan-6-ol acetate (2B) (116 mg, 0.49 mmol) and 7-benzyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (100 mg, 0.33 mmol) were dissolved in 2-propanol (20 ml) and triethylamine (0.68 ml, 4.9 mmol) and the mixture was subjected to micro waves (150° C., 6 bar, 300 W, 8 hours). The solvents were evaporated and the remaining was redissolved in dichloromethane (20 ml) and water (20 ml). The aqueous layer was acidified with potassium hydrogen sulfate until pH=2. The aqueous layer was separated and aqueous sodium hydroxide was added until pH=12. The aqueous layer was extracted with 3×50 ml of dichloromethane, and the combined organic material were added excess trifluoroacetic acid, and evaporated, to afford 123 mg of the title compound as a brown oil in 75% yield.

Workup

  1. customwas subjected to micro waves (150° C., 6 bar, 300 W, 8 hours)
  2. customThe solvents were evaporated
  3. dissolutionthe remaining was redissolved in dichloromethane (20 ml)
  4. customThe aqueous layer was separated
  5. additionaqueous sodium hydroxide was added until pH=12
  6. extractionThe aqueous layer was extracted with 3×50 ml of dichloromethane
  7. additionthe combined organic material were added excess trifluoroacetic acid
  8. customevaporated

Sources & evidence

ORD record
ord-9b6c61b507f94d2a93aca72cc5066565
Source dataset
uspto-grants-2007_06
Patent number
US07235538B2

Reaction notes

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