Triethylamine → HCID 15432862, compound

HRID 2297598Notes

Reaction equation

HRID 2297598 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH2:20]O)[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(Br)([Br:39])=O>ClCCl>[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH2:20][Br:39])[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68176Thionyl bromideHCID 15432861HCID 15432861, compound

Product 1

HCID 15432862HCID 15432862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.6 g of 6-benzyl-7-cyclopentyl-4-ethyl-2-hydroxymethyl-imidazo[4,5-e]-s-triazolo[1,5-a]pyrimidin-5-one are taken up in 7 ml of dichloromethane and 0.25 ml of triethylamine are added at ambient temperature with stirring. Then 0.15 ml of thionyl bromide are added. After 2 hours' stirring at constant temperature the reaction is complete. For working up, the mixture is diluted with 20 ml of dichloromethane and washed successively with 15 ml of water and 15 ml of aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and the solvent is distilled off in vacuo. The residue remaining is recrystallised from diethyl ether. 0.45 g of the title compound remain, pure enough to be used in the subsequent reactions.

Workup

  1. stirringAfter 2 hours' stirring at constant temperature the reaction
  2. washwashed successively with 15 ml of water and 15 ml of aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. distillationthe solvent is distilled off in vacuo
  5. customThe residue remaining is recrystallised from diethyl ether

Sources & evidence

ORD record
ord-b3b06a44a3a842d48d9515ac57abfcd0
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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