Methylamine → HCID 15617219, compound

HRID 2351698Notes

Reaction equation

HRID 2351698 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=C1)=O.CN>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([NH:23][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 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390205HCID 14390205, compound

Product 1

HCID 15617219HCID 15617219, compoundYield 70.8%

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), 1,1'-carbonyldiimidazole (2.9 g, 0.018 mole), and anhydrous tetrahydrofuran (200 ml) was stirred at room temperature with a stream of nitrogen bubbling through for 4 hours. The nitrogen flow was stopped and a solution of methylamine in tetrahydrofuran (36 ml of 1M) was added. The solution was stirred at room temperature under nitrogen for 1/2 hour. The reaction mixture was filtered and concentrated in vacuo and the residue triturated in water (100 ml) and filtered. The filter cake was recrystallized from tetrahydrofuran-isopropyl ether, giving 4.6 g (74%). Recrystallization from isopropyl alcohol-isopropyl ether gave 4.4 g of off-white needles, mp 199°-201° C.

Workup

  1. stirringThe solution was stirred at room temperature under nitrogen for 1/2 hour
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue triturated in water (100 ml)
  5. filtrationfiltered
  6. customThe filter cake was recrystallized from tetrahydrofuran-isopropyl ether
  7. customgiving 4.6 g (74%)
  8. customRecrystallization from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-2d350379cf644181ae120a5c25be412a
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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