Diisopropylethylamine → HCID 22482738, compound

HRID 2182069Notes

Reaction equation

HRID 2182069 reaction equation
Cl.[C:2]([C:5]1CNCCC=1)(=[O:4])[NH2:3].Cl[C:12]1[N:20]=[C:19]([CH3:21])[N:18]=[C:17]2[C:13]=1[N:14]([CH2:34][C:35]([NH2:37])=[O:36])[C:15](=[O:33])[N:16]2[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:23]=1[S:31][CH3:32].C([N:41]([CH:44]([CH3:46])C)[CH2:42][CH3:43])(C)C>C(O)C.O>[C:2]([C:5]1[CH2:46][CH2:44][N:41]([C:12]2[N:20]=[C:19]([CH3:21])[N:18]=[C:17]3[C:13]=2[N:14]([CH2:34][C:35]([NH2:37])=[O:36])[C:15](=[O:33])[N:16]3[C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][C:23]=2[S:31][CH3:32])[CH2:42][CH:43]=1)(=[O:4])[NH2:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 22482726HCID 22482726, compoundHCID 22482760HCID 22482760, compound

Product 1

HCID 22482738HCID 22482738, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

In 4 ml of ethanol, 0.16 g of 5-carbamoyl-1,2,3,6-tetrahydropyridine hydrochloride, 0.40 g of 2-[6-chloro-2-methyl-8-oxo-9-(4-isopropyl-2-methylthiophenyl)-8,9-dihydropurin-7-yl]acetamide, and 0.38 g of diisopropylethylamine were dissolved. Several drops of water were added thereto, and the reaction mixture was heated under reflux for 17 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol=7:1), followed by crystallization from ethyl acetate to yield 0.22 g of 2-[6-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2-methyl-8-oxo-9-(4-isopropyl-2-methylthiophenyl)-8,9-dihydropurin-7-yl]acetamide.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 17 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol=7:1)
  5. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-55bc475a9df64d3cb8b47a98ff63dbe9
Source dataset
uspto-grants-2005_05
Patent number
US06894168B2

Reaction notes

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