Tetrahydrofuran → HCID 14390224, compound

HRID 621904Notes

Reaction equation

HRID 621904 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:15]([CH2:16][C:17]([OH:19])=[O:18])[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:21].[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.[O:39]1[CH2:43][CH2:42]CC1>>[C:43]([OH:39])(=[O:21])/[CH:42]=[CH:16]/[C:17]([OH:19])=[O:18].[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:17](=[O:19])[CH2:16][N:15]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=[C:7]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 15617180HCID 15617180, compound

Product 1

HCID 14390224HCID 14390224, compound

Procedure

A solution of (2-(2-pyridinyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.00 g, 0.012 mole), 1,1'-carbonyldiimidazole (1.94 g, 0.012 mole), and anhydrous tetrahydrofuran (50 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 21/2 hours. The nitrogen flow was stopped, N-methylpiperazine (1.2 g, 0.012 mole) added, and the reaction mixture was stoppered and stirred over the weekend. The tetrahydrofuran was evaporated, water (100 ml) added, and the mixture basified with 10% sodium hydroxide solution. The mixture was extracted with ethyl acetate (4×25 ml). The combined organic extracts were washed with water (25 ml), dried over sodium sulfate, and concentrated in vacuo. The residue (1.3 g) was converted to the fumarate salt and crystallized from isopropyl alcohol-isopropyl ether-water, giving 1.4 g (26%). Recrystallization from isopropyl alcohol-isopropyl ether gave 1.2 g of a white solid, mp 212°-213° C.

Workup

  1. customThe tetrahydrofuran was evaporated
  2. additionwater (100 ml) added
  3. extractionThe mixture was extracted with ethyl acetate (4×25 ml)
  4. washThe combined organic extracts were washed with water (25 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customcrystallized from isopropyl alcohol-isopropyl ether-water
  8. customgiving 1.4 g (26%)
  9. customRecrystallization from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-240a2396bdb341bca791667b192c0ca7
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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