Diisopropylethylamine → HCID 22482738, compound

HRID 1359498Notes

Reaction equation

HRID 1359498 reaction equation
[C:1]([C:4]1CNCCC=1)(=[O:3])[NH2:2].Cl[C:11]1[N:19]=[C:18]([CH3:20])[N:17]=[C:16]2[C:12]=1[N:13]([CH2:33][C:34]([NH2:36])=[O:35])[C:14](=[O:32])[N:15]2[C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][C:22]=1[S:30][CH3:31].C([N:40]([CH:43]([CH3:45])C)[CH2:41][CH3:42])(C)C>C(O)C.O>[C:1]([C:4]1[CH2:45][CH2:43][N:40]([C:11]2[N:19]=[C:18]([CH3:20])[N:17]=[C:16]3[C:12]=2[N:13]([CH2:33][C:34]([NH2:36])=[O:35])[C:14](=[O:32])[N:15]3[C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][C:22]=2[S:30][CH3:31])[CH2:41][CH:42]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12069438HCID 12069438, compoundHCID 22482726HCID 22482726, compound

Product 1

HCID 22482738HCID 22482738, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

In 4 ml of ethanol, 0.16 g of 5-carbamoyl-1,2,3,6-tetrahydropyridine hydrochlioride, 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-9bba7de844c84b759c1f8f37438d4f17
Source dataset
uspto-grants-2003_07
Patent number
US06600038B1

Reaction notes

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