Dimethylamine → HCID 14390310, compound

HRID 2351699Notes

Reaction equation

HRID 2351699 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.[C:21](N1C=CN=C1)([N:23]1C=CN=[CH:24]1)=O.CNC>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([N:23]([CH3:24])[CH3:21])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390205HCID 14390205, compound

Product 1

HCID 14390310HCID 14390310, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(3-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (6.0 g, 0.018 mole), and 1,1'carbonyldiimidazole (2.9 g, 0.018 mole), in anhydrous tetrahydrofuran (175 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 4 hours. The nitrogen flow was stopped and a solution of dimethylamine in tetrahydrofuran (72 ml of 0.5M) was added. The solution was stirred at room temperature under nitrogen for 1/2 hour. The reaction mixture was filtered, concentrated in vacuo and the residue triturated in water (100 ml) and filtered. The filter cake was recrystallized from tetrahydrofuran-isopropyl ether, giving 4.5 g (70%). Recrystallization from isopropyl alcohol-isopropyl ether gave 4.0 g of cream colored needles, mp 144°-146° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue triturated in water (100 ml)
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from tetrahydrofuran-isopropyl ether
  6. customgiving 4.5 g (70%)
  7. customRecrystallization from isopropyl alcohol-isopropyl ether
  8. customgave 4.0 g of cream colored needles, mp 144°-146° C.

Sources & evidence

ORD record
ord-ad71449e4ab14182b5191955929699c0
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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