Isopropylamine → HCID 14390232, compound

HRID 2351653Notes

Reaction equation

HRID 2351653 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:33]([NH2:36])([CH3:35])[CH3:34]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:36][CH:33]([CH3:35])[CH3:34])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390232HCID 14390232, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-(4-chlorophenyl)3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.017 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.017 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 2 hours with a stream of nitrogen bubbling through it. A solution of isopropylamine (2.06 g, 0.035 mole) in tetrahydrofuran was added dropwise and the reaction mixture was allowed to stir at room temperature overnight. The tetrahydrofuran was evaporated and the solid residue was triturated with water. The solid was collected and dried under high vacuum overnight. The solid was recrystallized from isopropyl alcohol with cooling in the freezer, collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight to give 4.0 g (70%), mp 248°-9° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe tetrahydrofuran was evaporated
  3. customthe solid residue was triturated with water
  4. customThe solid was collected
  5. customdried under high vacuum overnight
  6. customThe solid was recrystallized from isopropyl alcohol
  7. temperaturewith cooling in the freezer
  8. filtrationcollected by filtration
  9. washwashed with water
  10. customdried under high vacuum at 50° C. overnight
  11. customto give 4.0 g (70%), mp 248°-9° C.

Sources & evidence

ORD record
ord-79aaa9b094d34be88c6601156b423804
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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