Dipropylamine → HCID 19898807, compound

HRID 1196499Notes

Reaction equation

HRID 1196499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([CH2:17][C:18]([OH:20])=O)=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH3:35]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]([CH2:17][C:18]([N:36]([CH2:37][CH2:38][CH3:39])[CH2:33][CH2:34][CH3:35])=[O:20])=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19898796HCID 19898796, compound

Product 1

HCID 19898807HCID 19898807, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.5 g (0.012 mole) of 2-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid and 3.2 g (0.015M) of 1,1'-carbonyldiimidazole (75%) in 150 ml of dry tetrahydrofuran was stirred under nitrogen for 30 minutes, then nitrogen was bubbled through the solution for 3 hours. The reaction mixture was treated with 1.2 g (0.012 mole) of dipropylamine and stirred for 16 hours. The reaction mixture was concentrated in vacuo. The crude residue was dissolved in 50 ml of methylene chloride and washed with water, saturated sodium bicarbonate, and again with water, then dried over magnesium sulfate and concentrated in vacuo to a solid residue (3.9 g). Recrystallization from 2-propyl ether:hexane yielded 3.4 g (76.4%) of pale yellow crystals, mp 104°-106° C.

Workup

  1. customnitrogen was bubbled through the solution for 3 hours
  2. stirringstirred for 16 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionThe crude residue was dissolved in 50 ml of methylene chloride
  5. washwashed with water, saturated sodium bicarbonate
  6. dry with materialagain with water, then dried over magnesium sulfate
  7. concentrationconcentrated in vacuo to a solid residue (3.9 g)
  8. customRecrystallization from 2-propyl ether

Sources & evidence

ORD record
ord-890955e26e6a4e15bcdd730fa346a093
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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